BR112012001940B1 - 2- (3-ALKYLTIOBENZOIL) CYCLOHEXANODIONS, HERBICIDE PRODUCTS, AND THEIR USE AS HERBICIDES - Google Patents

Description

(54) Title: 2- (3-ALKYLTIOBENZOIL) CYCLEHEXANODIONAS, HERBICIDIC PRODUCTS AND THEIR USE AS HERBICIDES (51) Int.CI .: C07C 317/24; C07C 323/22; A01N 31/16; A01N 41/10; A01N 10/31 (30) Unionist Priority: 7/29/2009 EP 09009777.5, 7/29/2009 US 61 / 229,365 (73) Holder (s): BAYER INTELLECTUAL PROPERTY GMBH (72) Inventor (s): HARTMUT AHRENS; ANDREAS VAN ALMSICK; JAN DITTGEN; CHRISTOPHER HUGH ROSINGER; ISOLDE HÀUSER-HAHN; STEFAN LEHR; DIETER FEUCHT

1/110 “2- (3-ALKYLBIOZENZOIL) CYCLEHEXANODIONAS, HERBICIDIC PRODUCTS AND THEIR USE AS HERBICIDES”

The invention relates to the technical area of herbicides, especially the technical area of herbicides for selective weed and weed control in crop plant cultures.

From different writings it is already known that certain benzoylcyclohexanediones have herbicidal properties. Thus are described in US 4,780,127, EP-A-338 992, EP-A-249 150 and EP-A-137963 the benzoylcyclohexanediones, which are replaced by different radicals in the phenyl ring.

However, the compounds known from those writings do not often show satisfactory herbicidal efficacy. The task of the present invention, therefore, is to provide other herbicidal compounds with improved properties - in relation to compounds known from the state of the art.

Benzoylcyclohexanediones, whose phenyl ring is replaced in position 2, 3 and 4 by selected radicals, have been found to be especially well suited as herbicides.

An object of the present invention is 2- (3-alkylthiobenzoyl) cyclohexanediones and their salts

O O X xk ^ so r ' R ⁴ ^ | | ^ R ² * fi * on what R ¹ means (C 1 -C 6) -alkyl, R ² means hydroxy, SR ¹³ , NR ¹⁴ R ¹⁵

R ³ and R ⁸ independently mean hydrogen or (C 1 -C 4) -alkyl, or the radicals R ³ and R ⁸ together form the unit Z, which represents an oxygen or sulfur atom, or represents one to four methylene groups,

R ⁴ and R ⁷ mean, independently of each other, hydrogen or (C 1 -C 4) -alkyl,

R ⁵ and R ⁶ mean, independently of each other, hydrogen or (C 1 -C 4) -alkyl, or form, together with the carbon atom to which they are attached, a carbonyl group,

X stands for OR ⁹ , OCOR ⁹ , OSO ₂ R ¹⁰ ,

R ⁹ means hydrogen, (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) -alkynyl, (C3C6) -cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl or phenyl- (C1-C6) -alkyl, in which the last six radicals mentioned are replaced by radicals from the group consisting of halogen, OR ¹¹ and S (O) _m R ¹² ,

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R ¹⁰ means (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) -alkynyl, (C3-C6) cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl or phenyl- (C1-C6) -alkyl, in which the last six radicals mentioned are replaced by radicals from the group consisting of halogen, OR ¹¹ and S (O) mR ¹² ,

R ¹¹ means hydrogen, (C1-C6) -alkyl, (C2-C6) -alkenyl or (C2-C6) -alkynyl,

R ¹² means (C1-C6) -alkyl, (C2-C6) -alkenyl or (C2-C6) -alkynyl,

R ¹³ stands for (C1-C4) -alkyl, phenyl substituted by radicals of the group consisting of nitro, cyano, (C1-C4) -alkyl, (C1-C4) -haloalkyl, (C1-C4) -alkoxy or (C1 -C4) -haloalkoxy or means partially or completely halogenated phenyl,

R ¹⁴ means hydrogen, (C1-C4) -alkyl or (C1-C4) -alkoxy,

R ¹⁵ means hydrogen or (C1-C4) -alkyl, or

R ¹⁴ and R ¹⁵ form, with the nitrogen atom to which they are attached, an unsaturated, partially saturated or saturated 5- or 6-membered ring, which contains zero, one or two other heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, which is replaced by radicals from the group consisting of cyano, halogen, (C1-C4) alkyl, (C1-C4) -haloalkyl, (C1-C4) -alkoxy and (C1-C4) -haloalkoxy,

Y means (C1-C6) -haloalkyl, m means 0, 1 or 2, n means 0, 1 or 2, s means 0, 1, 2 or 3.

In formula (I) and in all the following formulas, the alkyl radicals with more than two carbon atoms can be branched or be in a straight chain. Alkyl radicals mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl, hexyl, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl . Halogen means fluorine, chlorine, bromine or iodine.

If a group is replaced several times by radicals, then it must be understood that that group is replaced by one or more radicals mentioned, the same or different.

The compounds of the general formula (I) may exist, depending on the type of chain of the substituents, such as stereoisomers. If, for example, one or more asymmetrically substituted carbon atoms are present, then enantiomers and diastereomers can occur. Stereoisomers also occur when n means 1 (sulfoxides). Stereoisomers can be obtained from mixtures resulting during manufacture after usual separation methods, for example, by means of the chromatography separation method. Stereoisomers can also be manufactured through the use of stereoselective reactions by using adjuvants and / or optically active starting substances. The invention also relates to all stereoisomers and the

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3/110 their mixtures, which are covered by the general formula (I), however, are not defined specifically.

Preferred are compounds of the general formula (I), in which

R ¹ means methyl, ethyl, n-propyl or i-propyl,

R ² means hydroxy,

R ³ and R ⁸ mean, independently of each other, hydrogen or (C1-C4) -alkyl, or the radicals R ³ and R ⁸ together form a methylene or ethylene group,

R ⁴ and R ⁷ mean, independently of each other, hydrogen, methyl or ethyl,

R ⁵ and R ⁶ mean, independently of each other, hydrogen, methyl or ethyl,

X stands for OR ⁹ , OCOR ⁹ , OSO2R ¹⁰ ,

R ⁹ means cyclopropylmethyl or (C1-C6) -alkyl substituted by methoxy or ethoxy groups,

R ¹⁰ means (C1-C6) -alkyl substituted by methoxy or ethoxy groups,

Y means (C1-C3) -haloalkyl, n means 0, 1 or 2, s means 0, 1, 2 or 3.

Especially preferred are compounds of the general formula (I), in which

R ¹ means methyl, ethyl, n-propyl or i-propyl,

R ² means hydroxy,

R ³ and R ⁸ independently mean hydrogen, methyl or ethyl, or the radicals R ³ and R ⁸ together form a methylene or ethylene group,

R ⁴ and R ⁷ mean, independently of each other, hydrogen, methyl or ethyl,

R ⁵ and R ⁶ mean, independently of each other, hydrogen, methyl or ethyl,

X stands for OR ⁹ ,

R ⁹ means cyclopropylmethyl, or methyl or ethyl substituted by methoxy or ethoxy groups,

Y means trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoroisopropyl, n means 0, 1 or 2, s means 0, 1, 2 or 3.

In all the formulas cited below, the substituents and symbols have, unless otherwise defined, the same meaning, as described by formula (I).

Compounds according to the invention, where R ² means hydroxy, can be manufactured, for example, according to the methods indicated in scheme 1, by transforming a benzoic acid (II) into an acid chloride or an ester ( III), subsequently by means of a base reaction catalyzed with a cyclohexanedione (IV) and then by rearrangement in the presence of a cyanide source. Such methods

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4/110 are known to the skilled person and are described, for example, in WO 03/084912. In formula (III) L ¹ means chlorine, bromine or alkoxy.

Layout 1

(I SAW)

The cyclohexanediones of the formula (IV) are known can be manufactured, for example, according to the methods described in EP 0 338 992.

Compounds according to the invention, in which R ² means hydroxy for another radical, can be manufactured, according to scheme 2 and from the compounds according to the invention, in which R ² means hydroxy, by means of halogenation and by means of subsequent exchange reactions. Such reactions are known to the skilled person and are described, for example, in WO 03/084912.

Layout 2

(I) where R ² = OH

SO _n R

Y

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Benzoic acids (II) can be manufactured, for example, according to scheme 3, by means of reactions, known to the specialist, of the compounds (VI).

Layout 3

Compounds of formula (VI), where L ² means an ortho-directing substituent such as fluorine, can be metallized, for example, with lithium diisopropylamide and then transformed, with a thiolation reagent, into a compound of formula (VII). By means of another metallization reaction with n-butyl lithium, for example, and by means of subsequent carboxylation, benzoic acid (VIII) is reached. Such reactions are known from Tetrahedron Letters 1992 (33), 49, pages 7499-7502; J. Heterocyciclic Chem. 1999, 36, page 1453 ff. and Angew. Chem. 2005, 117, 380-398). The L ² radical is subsequently and eventually after esterification, replaced by the OR ⁹ radical. By reacting compounds (X) or (II) with oxidizing agents, such as meta-chloroperbenzoic acid, the thiol group is oxidized to a sulfinyl or sulfonyl group.

An exchange of group L ² by OR ⁹ can also be performed, according to scheme 4, in the stage of benzoylcyclohexanediones.

Layout 4

(XI)

(I) where R ² = OH and X = OR ⁹

The thiol radical can also be introduced in position 3, according to scheme 5, via metallization reactions of the compounds (VI). Such reactions are known from

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Synthesis 2006, 10, 1578 - 1589; Org. Lett. 8 (2006) 4, 765 - 768 and Angew. Chem. 2005, 117, 380-398.

Layout 5

(VI) (VII)

According to scheme 6, compounds (II), where X means hydroxy, can be converted to compounds (II), where X means OCOR ⁹ or OSO2R ¹⁰ , through acylation reactions. Such reactions are known from Huben-Weyl, Methoden der Organischen Chemie, publisher Georg Thieme, Sttutgart, volume VIII, fourth edition 1952, page 543 ff., As well as volume IX, fourth edition 1955, page 388 f.

Layout 6

The alkylthio radical in position 3 can be oxidized to sulfoxide or sulfone. For this, a variety of oxidation systems are offered, for example, peracids, such as meta-chloroperbenzoic acid, which is eventually generated in situ (for example, peracetic acid in the acetic acid / hydrogen peroxide / sodium tungstate system ( SAW)). Such reactions are known from Houben-Weyl, Methoden der Organischen Chemie, publisher Georg Thieme, Stuttgart, volume E 11, enhancement volumes for the fourth edition 1985, page 702 ff., Page 718 ff., As well as page 1194 ff . These oxidation reactions can also be carried out in the benzoylcyclohexanediones or corresponding enol esters stage, see diagram 7.

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ο

(V) with η = 0

(V) where η = 1,2

(I) where R ² = OH and η = 0 (I) where R ² = OH and n = 1, 2

It may be advantageous to exchange the sequence of the reaction steps described in the previous schemes or to combine them together. The reprocessing of the respective reaction mixtures occurs, in general, according to known methods, for example, by means of crystallization, reprocessing by aqueous extraction, by means of chromatography methods or by combinations of these methods.

The compounds of formula (II) are new and are also the subject of the present invention.

Series of compounds of formula (I) and / or their salts, which can be synthesized according to the reactions mentioned above, can also be manufactured in parallel, in which this can occur manually, partially automated or completely automated . In this process it is possible, for example, to automate the execution of the reaction, the reprocessing or the purification of the products or intermediates. In general, a procedure is understood below as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), publisher Wiley 1999, pages 1 to 34.

Regarding the parallelized execution of the reaction and reprocessing, a series of devices obtainable in the market can be used, for example, Calypso reaction blocks (Calypso reaction blocks), from Barnstead International, Dubuque, Iowa 52004-0797, USA, or reaction stations, from Radleys, Shirehill,

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Saffron Walden, Essex, CB 11 3AZ, England, or MultiPROBE Automated Workstations, by Perkin Elmar, Walham, Massachusetts 02451, USA. For the parallel purification of the compounds of the general formula (I) and their salts, or of the intermediates resulting from manufacture, other chromatography devices are available, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

The listed devices lead to a modular procedure, in which the individual work steps are automated, however, manual operations between the work steps must be performed. This can be avoided by using partial or complete use of integrated automation systems, in which the respective automation modules are operated by robots, for example. These types of automation systems can be obtained, for example, from the company Caliper, Hopkinton, MA 01748, USA.

The execution of one or several synthesis steps can be supported by the use of reagents supported by scavenger polymers / resins (cleaners). A number of test protocols are described in the technical literature, for example, in ChemFiles, volume 4. number 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

In addition to the methods described here, the manufacture of the compounds of the general formula (I) and their salts can occur, completely or partially, using methods supported by solid phases. To that end, the individual intermediates or all intermediates in the synthesis or a suitable synthesis for the respective procedure are bonded to a synthetic resin. Synthesis methods supported by solid phases are richly described in the technical literature, for example, Barry A. Bunin , in The Combinatorial Index, publisher Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (editor Günther Jung), publisher Wiley, 1999. The use of synthesis methods supported by solid phases allows a series of protocols known in the literature, which, again, can be performed manually or automatically. Reactions can be carried out, for example, using the microoreation technology IRORI (microreactors), from the company Nexus Biosystems, 12140, Community Road, Poway, CA92064, USA.

In both the liquid and solid phases, the execution of one or more synthesis steps can be facilitated by the use of microwave technology. A number of test protocols are described in the technical literature, for example, in Microwaves in Organic and Medicinal Chemistry (editor, C.O. Kappe and a. Stadler), Wiley publisher, 2005.

The manufacture according to the methods described here provides compounds of formula (I) and their salts in the form of series of substances, called libraries. Object of the present invention are also libraries, which contain at least two compounds of the formula (I) and their salts.

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The compounds according to the invention, of the formula (I), (and / or their salts), hereinafter referred to as "compounds according to the invention", have satisfactory herbicidal efficacy against a wide spectrum of important harmful plants, whether seasonal, mono and dicotyledonous. Even harmful perennial plants that are difficult to control, which sprout from rhizomes, rootstocks or other perennial organisms are well covered by the active substances.

Therefore, the object of the present invention is also a method for the control of unwanted plants or for the regulation of plant growth, preferably in cultivation plants, in which one or more compound (s) according to the invention are applied to plants (for example, noxious plants, such as mono and dicot weeds or unwanted crop plants), in the seeds (for example, grains, seeds or reproductive organisms, such as tubers or bud parts with buds), or on the surface on which the plants grow (for example, surface or cultivation area). In this sense, the compounds according to the invention can be applied, for example, in pre-sowing processes (possibly also by practice in the soil), pre-emergence or post-emergence. In some cases, mention is made, for example, of representatives of mono and dicotyledonous weed flora, which can be controlled by the compounds according to the invention, without a limitation relating to certain species having to occur, depending on the name.

Harmful monocotyledonous plants of the genera: Aegilops, Agropyron, Agrostis,

Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischall Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicot weed of the genera: Abutilon, Amaranthus, Ambrosia,

Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis,

Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanth.

When the compounds according to the invention are applied to the soil surface before germination, the germination of the weeds is completely prevented or the weeds grow to a germinated leaf stage, however, their growth is stopped and they die completely after the three to four weeks.

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When applying active substances to green parts of plants in the post-emergence process, growth stops after treatment and harmful plants remain in the existing growth stage at the point of application or die completely after a known period of time, so that in this way, competition from harmful weeds with crop plants is eliminated very early and in a sustainable manner.

Although the compounds according to the invention have a satisfactory herbicidal activity against mono and dicot weeds, cultivation plants of economically important crops, for example, dicot crops of the genera

Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or the monocotyledonous cultures of the genera Allium, Ananas, Aspar, Aspar, Aspar, , Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, depending on the structure of the respective compound according to the invention and its application rates, are not damaged in any way or only insignificantly. For these reasons, the present compounds are quite suitable for the selective control of unwanted plant growth in crop plants, such as crops of agroeconomic importance or ornamental plants.

In addition, the compounds according to the invention have surprising growth-regulating properties in relation to cultivation plants (depending on their respective structure and the rates of application employed). They interfere in a regulating manner in the exchange of substances from the plants themselves and, with this, they can be used in the objective interference in relation to the plant components and in relation to the facilitation of the harvest by causing dissection and stunted growth.

In addition, they are also suitable for general control and inhibition of unwanted vegetative growth, without thereby killing the plants. An inhibition of vegetative growth plays an important role in the case of several mono and dicotyledonous cultures, since, through this inhibition, a concentration can be reduced or totally prevented.

Due to their herbicidal and plant growth regulating properties, the active substances can also be used for the control of harmful plants in crops modified by genetic engineering or by conventional mutagenesis. Transgenic plants are generally characterized by particularly advantageous properties, for example, resistance against certain pesticides, especially against certain herbicides, resistance against plant diseases or the causes of plant diseases, such as certain plants insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern, for example,

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11/110 example, harvesting, this with regard to quantity, quality, storability, composition and special components. Thus, transgenic plants with increased starch content or altered starch qualities, or those with other fatty acid compositions from the crop are known.

In relation to transgenic crops, the application of the compounds according to the invention is preferable in crops of transgenic cultivation or economically significant ornamental plants, for example, in cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soy, canola, tomatoes, potatoes, tomatoes, peas and other types of vegetables. The compounds according to the invention can preferably be used as herbicides in crops of crop plants, which are resistant against the phytotoxic effects of the herbicides or which have been made resistant by genetic engineering.

The application of the compounds according to the invention or its salts is preferable in crops of transgenic cultivation or economically significant ornamental plants, for example, in cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soy, canola, tomatoes, potatoes, tomatoes, peas and other types of vegetables. The compounds according to the invention can preferably be used as herbicides in crops of crop plants, which are resistant against the phytotoxic effects of the herbicides or which have been made resistant by genetic engineering.

Conventional methods for the production of new plants, which have modified properties compared to plants previously existing, consist, for example, of traditional methods of cultivation and generation of mutants. Alternatively, new plants with modified properties can be generated using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). Transgenic cultivation plants have been described in several cases, for example by genetic engineering modifications of cultivation plants for the purpose of modifying the starch synthesized in plants (for example, WO 92/11376, WO 92/14827, WO 91/19806). , which are resistant to certain glufosinate-type herbicides (see, for example, EP-A30 A0242236, EP-A-A242246) or glyphosate (WO 92/00377) or sulfonylureas (EP-A0257993, US-A-5013659) , transgenic crop plants, for example, cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make plants resistant to certain pests (EP-A-0142924, EP-A-0193259). Transgenic crop plants with modified fatty acid composition (WO

91/13972). Cultivation plants modified by genetic engineering with new components or secondary substances, for example, new phytoalexins, which create an increased resistance to diseases (EPA 309862, EPA0464461). Modified plants

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12/110 by genetic engineering with reduced photorespiration, which have higher yields and greater tolerance to stress (EPA 0305398). Transgenic crop plants, which produce pharmaceutical proteins or important for diagnostic purposes ("molecular pharming"). Transgenic cultivation plants, which are characterized by higher yields or improved quality. Transgenic crop plants, which are characterized by a combination of the new properties mentioned above („gene stacking“).

Countless techniques of molecular biology, with which new transgenic plants, with modified properties, can be produced, are known at first; see, for example, Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Berlin Publisher, Heidelberg. or Christou, Trends in Plant Science 1 (1996) 423-431).

For these types of manipulation by genetic engineering, nucleic acid molecules are introduced into plasmids, which allow mutagenesis or sequential modification by recombination of DNA sequences. By means of standard methods, for example, base substitutions, partial sequences can be removed or natural or synthetic sequences can be added. To connect the DNA fragments to each other, adapters or linkers can be applied to the fragments, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory

Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker Gene und Klone, VCH Weinheim 2nd edition 1996.

The production of plant cells with reduced activity of a genetic product can be achieved by the expression of at least one corresponding antisense RNA, of a sense RNA to achieve a co-suppression effect or to achieve the expression of at least one suitable constructed ribozyme, which divides the specific transcripts of the aforementioned genetic product. In this regard, DNA molecules that comprise the complete coded sequence of a genetic product, including accompanying sequences that may be present, can be used, as well as DNA molecules that comprise only parts of the coded sequence, where those parts must be long as enough to cause an antisense effect on cells.

It is also possible to use DNA sequences, which have a high degree of homology to the coded sequences of a genetic product, but which are not completely identical.

In the case of the expression of nucleic acid molecules in plants, the synthesized protein is located in any compartment of the plant cell. However, in order to reach the location in a given compartment, the coded region can be

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13/110 connected with DNA sequences, which guarantee the location in a certain compartment. Such types of sequences are known to the skilled person (see, for example, Braun et al., Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106). Nucleic acid molecule expression can also occur in the organelles of plant cells.

The cells of transgenic plants can be regenerated, according to known techniques, for all plants. In the case of transgenic plants it may be, in particular, plants of any species of plants, that is, both monocotyledonous plants and also dicotyledonous plants.

Thus, transgenic plants are obtainable, which have properties modified by overexpression, suppression or inhibition of homologous (= natural) genes, or by gene sequences, or by the expression of heterologous (= foreign) genes, or gene sequences .

The compounds according to the invention can preferably be applied to transgenic cultures, which are resistant to growth substances, such as, for example, Dicamba, or against herbicides, which inhibit the essential enzymes of plants, for example, acetolactate synthase ( ALS) EPSP synthase, glutamine synthase (GS) or hydroxy phenyl pyruvate dioxigenase (HPPD), are resistant, respectively, to herbicides in the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and similar active substances.

When applying the active substances according to the invention in transgenic cultures, there are also, often and in addition to the effects against harmful plants, to be observed in other cultures, effects that are specific to the application in the respective transgenic culture, for example, a modified or specially extended spectrum of weeds, which can be controlled, modified application rates, which can be used for application, preferably combining ability with herbicides, against which the transgenic culture is resistant, as well as influencing the growth and yield of transgenic crop plants.

Therefore, the object of the invention is also the use of compounds according to the invention as herbicides for the control of harmful plants in transgenic crops.

The compounds according to the invention can be applied in the form of sprayable powders, emulsifiable concentrates, sprayable solutions, powders or granules in usual preparations. For this reason, object of the invention are also herbicidal products from 05/07/2018, p. 12/24

14/110 and plant growth regulators, which contain the compounds according to the invention.

The compounds according to the invention can be formulated in different ways, depending on which biological and / or chemical-physical parameters are previously given. As formulation possibilities are in question: post-sprayable (WP), post-soluble in water (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as water-in-oil and oil-in-water emulsions, dispersions based on oil or water, mixable solutions in oil, suspensions in capsules (CS), POWDER (DP), paint strippers, granules for application to the soil or spreading application, water-dispersible granules (WG), water-soluble granules (SG ), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, WinnackerKüchler, Chemische Technologie, Volume 7, C. Hanser publishers, Munich, 4th edition 1986; Wade van Valkenburg, Pesticide Formulations, Marcel Dekker, NY, 1973; K. Martens, Spray Drying Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

Necessary formulation aids, such as inert materials, surfactants, solvents and other additional substances are also known and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, Introduction to Clay Colloid Chemistry; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, Solvents Guide; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, Grenzflachenaktive Athylenoxidaddukte, Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, Chemische Technologie, volume 7, publisher C. Hanser Munich, 4th edition 1986.

Based on these formulations, combinations with other substances with pesticidal efficacy are also possible, such as insecticides, acaricides, herbicides, fungicides, as well as protective agents, fertilizers and / or growth regulators, in the form of a ready formulation or as tank mix.

Sprayable powders are prepared uniformly dispersible in water, which, in addition to an inert substance or a diluent outside the active substance, or to ionic and / or non-ionic surfactants (humectants, dispersants), contain, for example, polyoxyethylated alkylphenols , polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, polyglycol sulphate, fatty alcohol ether, alkanesulphonate, sodium alkylbenzolsulphonate sodium lignosulfonate, sodium 2,2'-dinaftymethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium acid. For the manufacture of powder powders the herbicidal active substances are finely ground from 05/07/2018, p. 12/25

15/110 in usual devices such as hammer mills, fan mills and air jet mills or are subsequently mixed with the formulation adjuvants.

Emulsifiable concentrates are manufactured by dissolving the active substance in an organic solvent, for example, butanol, cyclohexane, dimethylformamide, xylol, or also aromatics with a high boiling point, or hydrocarbons, or mixtures of organic solvents using one or more surfactants of the type ionic and / or non-ionic (emulsifiers). Emulsifiers can be used, for example: calcium salts of alkylarylsulfonic acid, such as calcium from dodecylbenzolsulfonate, or non-ionic emulsifiers, such as polyglycolester of fatty acid, alkylarylpolyglycolether, polyglycolester of fatty alcohol, condensation products of ethylene oxides or propylene oxide, alkyl polyether, sorbinate esters, such as, for example, fatty acid sorbinate ester or polyoxyethylene sorbinate ester, such as, for example, fatty acid polyoxyethylene sorbinate ester.

Powders are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water or oil based. They can be manufactured, for example, by wet grinding through commercially available hammer mills and eventually by using surfactants, as these are listed above in the case of other types of formulation.

Emulsions, for example, oil in water (EW) emulsions can be manufactured, for example, by agitators, colloid mills and / or static mixers, by using aqueous organic solvents and possibly surfactants, as they are already listed above in the case other types of formulation.

Granules can be made either by spraying the active substance onto the granular inert material or capable of absorbing, or by applying active substance concentrates through adhesives, for example, polyvinyl alcohol, polyacrylic acid sodium or also mineral oils, on the surface of carrier materials, such as sand, kaolinite or inert granular materials. Suitable active substances can also be granulated in the usual manner for the manufacture of fertilizer granules - optionally in admixture with fertilizers.

Water-dispersible granules are generally manufactured according to usual methods, such as jet drying, fluidized bed granulation, disc granulation, mixing as a high-speed mixer and extrusion without solid inert material.

For the manufacture of disc granules, in fluidized bed, by extrusion or jet, see, for example, methods in Spray-Drying Handbook ”3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, Agglomeration, Chemical and Engineering 1967, pages 147 ff;

of 05/07/2018, p. 12/26

1/16

Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-HilI, New York 1973, pages. 8-57.

For other details regarding the formulation of plant protection agents, see, for example, GC Klingman, 'Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, 'Weed Control Handbook, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

Agrochemical preparations generally contain 0.1 to 99% by weight, especially 0.1 to 95% by weight of compounds according to the invention. In sprayable powders the concentration of active substances is about 10 to 90% by weight, for example, the radical for the 100% by weight consists of usual components of the formulation. In the case of emulsifiable concentrates the concentration of active substances is about 1 to 90, preferably 5 to 80% by weight. Formulations in powder form contain 1 to 30% by weight of active substance, preferably, in most cases, contain 5 to 20% by weight of active substance, sprayable solutions contain about 0.05 to 80, preferably 20 to 50% by weight of active substance. In the case of water-dispersible granules, the active substance content depends, in part, on whether the effective compound is present in a solid or liquid form and on which granulation aids, fillers etc. will be used. In the case of water-dispersible granules, the active substance content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the formulations of active substances mentioned may contain the respective adhesives, humectants, dispersants, emulsifiers, adhesion-promoting agents, preservatives, antifreeze and solvents, fillers, transport substances and dyes, foams, evaporation inhibitors and the pH value and the agent that interferes with viscosity.

Based on these formulations the combinations can also be made with other substances of pesticidal efficacy, such as, for example, insecticides, acaricides, herbicides, fungicides, as well as protective agents, fertilizers and / or growth regulators, for example, in the form of a ready-made formulation or as a tank mix.

Combination partners for the compounds according to the invention in mixing or tank mix formulations are known, for example, active substances, which are usable and are based on inhibition of acetolactate synthase, for example, acetyl-CoA-carboxylase , cellulose synthase, enolpyruvyl chiquimate-3-phosphate synthase, glutamine synthase, p-hydroxy phenyl pyruvate-dioxigenase, phytendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as they are described, for example, from Weed Research 26 (1986) 441-445 or The Pesticide Manual, 14th edition, The British Crop Protection Council and the Royal Soc. Of Chemistry, 2003 and the literature cited from 05/07/2018, p. 12/27

17/110 there. As known herbicides or plant growth regulators, which can be combined with the compounds according to the invention, the following active substances are named, for example (the compounds are designated or with the common name “common name”, as the International Organization for Standardization (ISO), or with the chemical name, or with the code number) and invariably comprise all forms of application, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. In this sense, for example, one and, in part, several forms of application are cited:

Acetochlor, Acibenzolar, Acibenzolar-S-methyl, Acifluorfen, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxidim, Alloxidine-sodium, Ametrin, Amicarbazone, Amidochlor, Amidosulfuron, Aminocyclopyridine, Anhydrous, Amino-amide, Amino-amide, Anhydrous Asulam, Atrazine, Azafenidin, Azimsulfurone, Aziprotrin, BAH043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H,

Beflubutamide, Benazolin, Benazolin-ethyl, Bencarbazone, Benfluralin, Benfuresate, Bensulide, Bensulfurone-methyl, Bentazone, Benzfendizone, Benzobicyclon, Benzofenap, Benzofluoro, Benzoilprop, Bicyclopyrone, Biphenoxyl, Bisacyl, Bisacil Bromobutide, Bromophenoxy, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor, Butafenacil, Butamiphos, Butenachlor, Butralin, Butroxidim, Butylate, Cafenstrole, Carbetamide, Carfentrazone, Clafentor, Cliforazone, Cliforazone, Cliforazone, Cliforazone Clorfenac, Clorfenac-sodium, Clorfenprop, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chloroquat-chloride, Chlornitrofen, Chlorophthalin, Chloro-dimethyl, Chlorohydron, Cinchulfonidone, Chlorohydron, Cinlorulfone Clodinafop Clodinafop-propargil, Clofencet, Clomazona, Clomeprop, Cloprop, Clopiralid, Cloransulam, Cloransulam-methyl, Cumiluron, Cyanamide, Cyanazine, Cicl anilide, Cicloate, Ciclosulfamuron, Cicloxidim, Cicluron, Cihalofop, Cihalofop-butyl, Ciperquat, Ciprazina, Ciprazol, 2,4-D, 2,4-DB, Daimuron / Dimron, Dalapon, Daminozide, Dazomet, n-Decanol, Desmedifam, Desmetrin, Detosil-Pyrazolate (DTP), Diallate, Dicamba, Diclobenil, Diclorprop, Diclorprop-P, Diclofop, Diclofop-methyl, Diclofop-P-methyl, Diclosulam, Dietathyl, Diethyl-ethyl, Difenoxuron, Difenzufir, Difenzoquatl, Difenzoquatl, Difenzo -sodium, Dimefuron, Diquegulac-sodium, Dimefuron, Dimepiperate, Dimetachlor, Dimetametrin, Dimetenamide, Dimetenamide-P, Dimetipin, Dimetrasulfuron, Dinitramine, Dinoseb, Dinoterb, Difenamid, Dipropetrin, Diquat, Diquaty, Diquatit, Diquaty -ethyl, Endotal, EPTC, Esprocarb, Etalfluralin, Etametsulfuron-methyl, Etefon, Etidimuron, Etiozin, Etofumesate, Etoxifen, Etoxifen-ethyl, Etoxisulfuron, Etobenzanid, F5331, that is, N- [2-cor-2-cor - [4- (3fluoropropyl) -4,5-dihydro-5-oxo-1-H-tetrazol-1-yl] phenyl] -ethanesulfonamide, Fenoprop, F enoxaprop, Fenoxaprop-P, Fenoxaprop-ethyl, from 05/07/2018, p. 12/28

1/18

Fenoxaprop-P-ethyl, Fenoxasulfone, Fentrazamide, Fenuron, Flamprop, Flamprop-Misopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazifopbutil, Fluazifop-P-butyl, Fluazolate, Flucarbazona, Flucarbazona Flucetosulfurone, Flucloralin, Flufenacet (Tiafluamide), Flufenpir, Flufenpir-ethyl, Flumetralin, Flumetsulam,

Flumiclorac, Flumiclorac-pentil, Flumioxazin, Flumipropin, Fluometuron, Fluorodifen, Fluoroglycophen, Fluoroglycophen-ethyl, Flupoxam, Flupropacil, Flupropanate, Flupirsulfuron, Flupirsulfuron-methyl-sodium, Fluryrururon, Fluridurur, Flurenurur, Flurenurur, Fluren, Flurprimidol, Flurtamone, Flutiacet, Flutiacet-methyl, Flutiamide, Fomesafen, Foramsulfuron, Forclorfenuron, Fosamine, Furiloxifen, Gibberellic acid, Glufosinate, L10 Glufosinate, L-Glufosinate-ammonium, Glufosinate, Glifosinate, 9 Halosulfuron, Halosulfuron-methyl, Haloxifop, Haloxifop-P, Haloxifop-ethoxyethyl, Haloxifop-P-ethoxyethyl, Haloxifop-methyl, Haloxifop-P-methyl, Hexazinone, HNPC-9908, HOK-201, HW-02, Imazametabenz methyl, Imazamox, Imazapic, Imazapir, Imazaquin, Imazetapir, Imazosulfuron, Inabenfide,

Indanofan, Indaziflam, Indole acetic acid (IAA), 4-Indol-3-yl butyric acid (IBA), lodosulfuron, lodosulfuron-methyl-sodium, Ioxynil, Ipfencarbazone, Isocarbamide, Isopropalin, Isoproturon, Isoxole, Isoxlur, , Isoxapirifop, IDH-100, KUH-043, KUH-071, Carbutilate, Cetospiradox, Lactofen, Lenacil, Linuron, Maleic acid hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and-sodium, Mecoprop, Mecoprop-sodium, Mecoprop20 butotyl, Mecoprop-P-butotil, Mecoprop-P-dimethylammonium, Mecoprop-P-2-ethylhexil, MecopropP-potassium, Mefenacet, Mefluidide, Mepiquat-chloride, Mesosulfuron, Mesosulfuron-methyl, Mesotrione, Metabione, Metabenzam, , Metazachlor, Metazosulfuron, Metazole, Metiozolin, Methoxyfenon, Metildimron, 1-Methylcyclopropen, Methylisothiocyanate, Metobenzuron, Metobenzuron, Metobromuron, Metolachlor, S25 Metolachlor, Metosulam, Metoxuron, Moletho- dihydrogensulfate, Mono linuron, Monosulfuron, Monuron, MT 128, MT-5950, that is, N- [3-chloro-4- (1-methylethyl) -phenyl] -2-methylpentanamide, NGGC-011, Naproanilide, Napropamide, Naptalam, NC- 310, that is, 4- (2,4dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole, Neburon, Nicosulfuron, Nipiraclofen, Nitralin,

Nitrofen, Nitrofenolat-sodium (isomer mixture), Nitrofluorfen, nonanoic acid, Norflurazon, Orbencarb, Ortosulfamuron, Orizalin, Oxadiargil, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxifluorfen, Paclobutrazol, Paraquatalichol, Para , Pendralin, Penoxsulam, Pentanochlor, Pentoxazone, Perfluidone, Petoxamide, Fenisofam, Fenmedifam, Fenmedifam-ethyl,

Picloram, Picolinafen, Pinoxaden, Piperophos, Pirifenop, Pirifenop-butyl, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Probenazol, Profluazole, Prociazine, Prodiamine, Prifluralin, Profoxidim, Prohexadone, Prohexadione, Prohexadione, Prohexadione,

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1/1910

Prometrin, Propachlor, Propanil, Propaquizafop, Propazin, Profam, Propisochlor, Propoxycarbazone, Propoxycarbazone-sodium, Propyrisulfuron, Propizamide, Prosulfalin, Prosulfocarb, Prosulfuron, Prinachloro, Piraclonil, Piraflufen, Pirafluren, Piraflurol, Pirafluren , Pirazoxifen, Piribambenz, Piribambenz5 isopropil, Piribenzoxim, Piributicarb, Piridafol, Piridate, Piriftalid, Piriminobac, Piriminobacmetil, Pirimisulfan, Piritiobac, Piritiobac-sodium, Piroxasulfone, Piroxsulam, Quincloral, Quiz, Quincloral, Quincloral, Quiz, Quincloral, Quiz, Quincloral, Quin Quizalofop-P-ethyl, Quizalofop-P-tefuril, Rimsulfuron, Saflufenacil, Secbumeton, Setoxidim, Siduron, Simazine, Simetrin, SN-106279, Sulcotrione, Sulfalate (CDEC), Sulfentrazone, Sulfometuron,

Sulfometuron-methyl, Sulfosate (Glyphosate-trimesium), Sulfosulfuron, SIN-523, SIP-249, SIP298, SIP-300, Tebutam, Tebutiuron, Tecnazena, Tefuriltrione, Tembotrione, Tepraloxidim, Terbacil, Terbucarb, Terbucarb, Terbucarb, Terbucarb, Terbucarb, Terbucarb, Terbucarb , TH-547, Thenylchlorine, Thiafluamide, Tiazafluron, Tiazopir, Tidiazimin, Tidiazuron, Tiencarbazone, Tiencarbazonamethyl, Tifensulfurone, Tifensulfuron-methyl, Thiobencarbe, Tiocarbazil, Topramezona, Topramezona

Tralcoxidim, Trialato, Triasulfuron, Triaziflam, Triazofenamide, Tribenuron, Tribenuronmetil, tricolor acetic acid (TCA), Triclopir, Tridifane, Trietazine, Trifloxisulfuron, Trifloxysulfuron, Triflural, Triflural, Triflural, Triflural, Triflural, Triflural, Triflural, Triflural , Tsitodef, Uniconazol, Uniconazol-P, Vernolate, ZJ-0166, ZJ0270, ZJ-0543, ZJ-0862, as well as the following compounds:

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1/20

For application, the formulations present in the commercially available form are eventually diluted in the usual manner, for example, in sprayable powders, emulsifiable concentrates, dispersions and granules dispersible in water by means of water. Preparations in the form of powders, spreading granules or soil, as well as sprayable solutions are usually no longer diluted, before application, with other inert substances.

With external conditions such as temperature, humidity, the type of herbicide used, among other things, varies the required rate of application of the compounds of formula (I). It can vary within other limits, for example, between 0.001 and 1.0 kg / ha or more of active substance, however, it is preferably between 0.005 and 750 g / ha.

The following examples explain the invention.

A. Chemical examples

2- (2-methoxy-3-methylsulfinyl-4- (trifluormethyl) benzoyl) cyclohexane-1,3-dione (Example in table number 1-17)

Step 1: synthesis of 1-fluorine-2-methylthio-3- (trifluoromethyl) benzol

Under an atmosphere of inert gas, 32.8 ml (1.6M in hexane. 52.5 mmol) of n-butyllithium were dripped into a solution cooled to 0 ° C of 7.77 ml (55 mmol) of diisopropylamine in 100 ml of THF free of water and the solution was cooled after 10 minutes of stirring at 78 ° C. At that temperature, 8.21 g (50 mmol) of 3-fluorbenzotrifluoreton were added and the reaction mixture was stirred for one hour at that temperature. Then 4.21 ml (55 mmol) of dimethylsulfide were dripped. The reaction mixture heated up within about three hours at room temperature (RT), then it was cooled again to 0 ° C. At that temperature, 10 ml of water were added by dripping and the reaction mixture was reduced to about% of its volume. The residue was taken up in water and dichloromethane, the phases were separated and the organic phase was successively washed with water, 10% hydrochloric acid, water, saturated aqueous NaHCO3 solution, water and saturated aqueous NaCl solution and was dried and filtered through of sodium sulfate. The solvent was separated and the residue was rectified in vacuo. 8 g of 1-fluorine-2methylthio-3- (trifluoromethyl) benzol with a boiling point of 68 ° C at 6 mm Hg were obtained.

Step 2: synthesis of 2-fluorine-3-methylthio-4- (trifluoromethyl) benzoic acid

Under an atmosphere of inert gas, 27.5 ml (1.6 M in hexane, 44 mmol) of n-butyllithium were dripped into a cooled solution to -78 ° C of 7.98 g (38 mmol) of 1-fluorine-2-methylthio -3 (trifluormethyl) benzol in 60 ml of water-free THF, where the temperature of the reaction mixture should not exceed -65 ° C. The mixture was stirred for 3 hours at -78 ° C and then a stream of carbon dioxide was passed at that temperature, so that the temperature of the reaction mixture did not exceed -45 ° C. Then the mixture was warmed to room temperature and then cooled again to 0 ° C. To

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21/110 reprocessing was added, at this temperature and dripped, enough water, until the precipitation formed dissolved. Diethyl ether was added and the organic phase was extracted three times with water. The combined aqueous phases were acidified with 10% hydrochloric acid. The aqueous phase was extracted several times with dichloromethane, the combined organic phases were washed with saturated aqueous NaCl solution, dried over sodium sulfate and the filtrate was finally released from the solvent. The crude product obtained in this way was recrystallized from benzine (80110 ° C) / acetic acid ethyl ester. 6.8 g of 2-fluor-3-methylthio-4 (trifluoromethyl) benzoic acid were obtained.

Step 3: synthesis of benzoic acid 2-fluor-3-methylthio-4- (trifluoromethyl) methylester

20.0 g (78.7 mmol) of benzoic acid 2-fluoro-3-methylthio-4- (trifluoromethyl) methylester were placed in 200 ml of methanol with 5 ml of sulfuric acid and the mixture was heated sufficiently by reflux , until it showed a complete conversion HPLC analysis. The mixture was cooled and the solvent was removed. The residue was taken up in water and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed once with saturated aqueous NaHCO3 solution. Then the organic phase was dried and the filtrate was concentrated. 20.5 g of benzoic acid 2-fluoro-3-methylthio-4- (trifluoromethyl) methylester were obtained.

Step 4: synthesis of benzoic acid 2-methoxy-3-methylthio-4- (trifluoromethyl) methylester

A mixture of 19.9 g (74.2 mmol) of benzoic acid 2-fluoro-3-methylthio-4- (trifluoromethyl) methylester and 40.1 g (30% by weight, 223 mmol) of sodium methylate was added. heated in 250 ml of methanol for 6 hours by reflux. For reprocessing the mixture was concentrated on a rotary evaporator, the residue was taken up in water and the mixture was extracted with dichloromethane. The organic phase was dried and the filtrate was freed from the solvent.

As a residue, 15.9 g of benzoic acid 2-methoxy-3-methylthio-4- (trifluoromethyl) methylester were obtained. The aqueous phase of the extractive reprocessing was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and the filtrate was freed from the solvent. As a residue, 3.80 g of 2-methoxy-3-methylthio-4- (trifluoromethyl) methyl ester of benzoic acid were obtained in addition.

Step 5: synthesis of benzoic acid 2-methoxy-3-methylthio-4- (trifluoromethyl) methylester (Example from table number 12-13)

16.0 g (57.1 mmol) of benzoic acid 2-methoxy-3-methylthio-4- (trifluoromethyl) methylester were placed in 160 ml of methanol with 16 ml, 20%, of sodium hydroxide solution and stirred for 4 hours at room temperature. For reprocessing the mixture was released from the solvent and the residue was taken up in a little water. The mixture was cooled in an ice bath and then acidified with dilute hydrochloric acid. The mixture

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22/110 was stirred for 5 minutes and at room temperature, then the contents were filtered. 15.3 g of 2-methoxy-3-methylthio-4- (trifluoromethyl) benzoic acid were obtained

Step 6: synthesis of 3- (2-methoxy-3-methylthio-4- (trifluormethyl) benzoyloxy) -cyclohex-2enone

200 mg (78% by weight of purity, 0.59 mmol) of 2-methoxy-3-methylthio-4 (trifluoromethyl) benzoic acid were placed in 20 ml of dichloromethane, successively with 133 mg (1.05 mmol) of chloride oxalic acid and three drops of NN-dimethylformamide. After the end of the gas separation, the mixture was still heated for 10 minutes by reflux. Then the contents were cooled to room temperature and released from the solvent. The residue was placed in 20 ml of dry dichloromethane with 93 mg (0.83 mmol) of 1,3-cyclohexanedione, then 152 mg (1.50 mmol) of triethylamine were added dropwise. The mixture was stirred for 16 hours at room temperature. For reprocessing, the contents were filled with 3 ml of 1M hydrochloric acid. After the separation phase, the organic phase was released from the solvent. The residue was purified by chromatography, whereby 100 mg of 3- (2-methoxy-3-methylthio-4- (trifluormethyl) benzoyloxy) cyclohex-2-enone were isolated.

Step 7: synthesis of 3- (2-methoxy-3-methylsulfinyl-4- (trifluormethyl) benzoyloxy) -cyclohex-2enone

100 mg (0.28 mmol) of 3- (2-methoxy-3-methylsulfinyl-4- (trifluormethyl) benzoyloxy) 20 cyclohex-2-enone was placed in 10 ml of dichloromethane with 68 mg (70% by weight, 0 , 28 mmol) of perbenzoic acid meta-chlorine. The mixture was stirred for 1 hour at room temperature. For reprocessing, 3 ml, 10%, of sodium hydrosulfite solution were placed. After demonstrating the absence of peroxides, the organic phase was washed twice with corresponding 5 ml of saturated aqueous solution of

NaHCO3. After phase separation the solvent was removed. 90 mg of 3 (2-methoxy-3-methylsulfinyl-4- (trifluormethyl) benzoyloxy) -cyclohex-2-enone were isolated.

Step 8: synthesis of 2- (2-methoxy-3-methylsulfinyl-4- (trifluormethyl (benzoyl) cyclohexan-1,3-dion (example from table number 1-17) mg (0.24 mmol) of 3- ( 2-methoxy-3-methylsulfinyl-4- (trifluormethyl) benzoyloxy) -cyclohex30 2-enone was placed in 15 ml of acetonitrile and successively with 48 mg (0.48 mmol) of triethylamine, as well as eight drops of trimethylsilyl cyanide. The mixture was stirred for 16 hours at room temperature, the solvent was separated for reprocessing, the residue was taken up in 15 ml of dichloromethane and placed with 30 ml of 1N hydrochloric acid. After the phase separation the solvent was separated and the The residue was purified by chromatography, whereby 49.9 mg of 2- (2-methoxy-3-methylsulfinyl-4 (trifluormethyl (benzoyl) -cyclohexan-1,3-dion were obtained.

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1/23

The examples listed in the following tables have been manufactured analogously to the methods mentioned above or are obtainable analogously to the methods mentioned above. These compounds are very especially preferred.

The abbreviations used mean:

Et = ethyl Me = methyl Pr = propyl Ph = phenyl

Table 1: compounds according to the invention, of the general formula (I), in which R ² means hydroxy and R ³ to R ⁸ mean, respectively, hydrogen.

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-1 DH Me 0 cf ₃ 1-2 OH Et 0 cf ₃ 1-3 OH n-Pr 0 cf ₃ 1-4 OH i-Pr 0 cf ₃ 1-5 OH Me 1 cf ₃ 1-6 OH Et 1 cf ₃ 1-7 OH n-Pr 1 CFj 1-8 OH i-Pr 1 CFj 1-9 OH Me 2 cf ₃ 1-10 OH Et 2 cf ₃ 1-11 OH n-Pr 2 cf ₃ 1-12 OH i-Pr 2 cf ₃ 1-13 OMe Me 0 cf ₃ 16.93 (s, 1H), 7.49 (d, 1H), 7.1 S (d, 1H), 3.86 (s, 3H), 2.78 (t, 2H) ₍ 2.43 (t, 2H), 2.42 (S. 3H). 2.06 (quint, 2H) 1-14 OMe Et 0 cf ₃ 1-15 OMe n-Pr 0 cf ₃ 1-16 OMe i-Pr 0 cf ₃ 1-17 OMe Me 1 cf ₃ 16.66 (s, 1H), 7.56 (d, 1H), 7.42 (d, 1H), 3.88 (s, 3H), 3 07 (s, 3H), 281 (m, 2H), 2.46 (m, 2H), 2.08 (ΠΊ, 2H> 1-18 OMe Et 1 cf ₃ 1-19 OMe n-Pr 1 cf ₃ 1-20 OMe i-Pr 1 cf ₃ 1-21 OMe Me 2 cf ₃ 16.67 {ε. 1H), 7.71 (d, 1H), 7.51 (d, 1H), 3.84 (s, 3H), 3.30 <s, 3H), 2.82 (t, 2H) „2.44 (t, 2H), 2.08 (quint, 2H) 1-22 OMe Et 2 cf ₃ 1-23 OMe n-Pr 2 cf ₃

Petition 870180037453, of 05/07/2018, p. 12/34

24/110

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-24 OMe i-Pr 2 cf ₃ 1-25 OEt Me 0 cf ₃ 16.82 (s, 1H), 7.47 (d, 1H). 7.22 (d, 1H), 4.03 (q, 2H}, 2.76 (t, 2H), 2.46 - 2-41 (m. 5H), 2.06 (quint, 2H). 1.30 (t, 3H) 1-26 OEt Et 0 cf ₃ 1-27 OEt n-Pr 0 cf ₃ 1-2S OEt í-Pr 0 cf ₃ 1-29 OEt Me 1 cf ₃ 16.66 (s, 1H), 7.55 (d, 1H), 7.41 (d „1H), 4.30 (m, 1H), 3.78 (m _r 1 H>, 3 06 (s, 3H). 2.80 (m, 2H) , 2.52 (m, 1H), 2.39 (m, 1H), 2.07 (m, 2H), 1.32 (t. 3H) 1-30 OEt Et 1 cf ₃ 1-31 OEt n-Pr 1 cf ₃ 1-32 OEt i-Pr 1 cf ₃ 1-33 OEt Me 2 cf ₃ 16.63 (5, 1H), 7.71 (d, 1H), 7.51 (d, 1H}, 4.01 (m, 2HJ. 3.32 (s, 3H), 2.81 (t, 2K), 2.44 (t, 2H), 2.07 (quint, 2H), 1.32 (t, 3H) 1-34 OEt Et 2 cf ₃ 1-35 OEt n-Pr 2 cf ₃ 1-36 OEt i-Pr 2 cf ₃ 1-37 O-CHj.c-Pr Me 0 cf ₃ 1-38 O-CHj.c-Pr Et 0 cf ₃ 1-39 O-CHj.c-Pr n-Pr 0 CFj 1-40 O-CH ₂ .c-Pr i-Pr 0 cf ₃ 1-41 O-CHj.c-Pr Me 1 cf ₃ 1-42 O-CH ₂ .c-Pr Et 1 cf ₃ 1-43 O-CH ₂ .c-Pr n-Pr 1 CFs 1-44 O-CHí.c-Pr i-Pr 1 cf ₃ 1-45 O-CHj.c-Pr Me 2 cf ₃ 1-46 O-CH ₂ .c-Pr Et 2 cf ₃ 1-47 O-CH ₂ .c-Pr n-Pr 2 cf ₃ 1-4Θ O-CH ₂ c-Pr i-Pr 2 cf ₃ 1-49 OCH _? CH ₂ OMe Me 0 cf ₃ 1-50 OCH ₂ CH ₂ OMe Et 0 cf ₃ 1-51 OCHjCHjOMe n-Pr 0 cf ₃

Petition 870180037453, of 05/07/2018, p. 12/35

25/110

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-52 OCH ₂ CH ₂ OMe i-Pr 0 cf ₃ 1-53 OCHiCHiOMe Me 1 cf ₃ 1-54 OCH ₂ CH ₂ OMe Et 1 cf ₃ 1-55 OCH ₂ CH ₂ OMe n-Pr 1 cf ₃ 1-56 OCH ₂ CH ₂ OMe i-Pr 1 cf ₃ 1-57 OCH ₃ CH ₂ OMe Me 2 cf ₃ 1-58 OCHjCHjOMe Et 2 cf ₃ 1-59 OCH ₂ CH ₂ OMe n-Pr 2 cf ₃ 1-60 OCH ₂ CH ₂ OMe i-Pr 2 cf ₃ 1-61 OCH ₂ CH ₂ SMe Me 0 cf ₃ 1-62 OCH ₂ CH ₂ SMe Et 0 cf ₃ 1-63 OCH ₂ CH ₂ SMe n-Pr 0 cf ₃ 1-64 OCH ₂ CH ₂ SMe i-Pr 0 cf ₃ 1-65 OCHjCHjSMe Me 1 cf ₃ 1-66 OCH ₂ CH ₂ SMe Et 1 CF _a 1-67 OCH ₂ CH ₂ SMe n-Pr 1 CF _a 1-68 OCH ₂ CH ₂ SMe i-Pr 1 cf ₃ 1-69 OCH ₂ CH ₂ SMe Me 2 cf ₃ 1-70 OCH ₂ CH ₂ SMe Et 2 cf ₃ 1-71 OCH ₂ CH ₂ SMe n-Pr 2 cf ₃ 1-72 OCH ₂ CH ₂ SMe i-Pr 2 cf ₃ 1-73 OCH ₂ CH ₂ S0 ₂ Me Me 0 cf ₃ 1-74 OCH ₂ CH ₂ SO ₂ Me Et 0 cf ₃ 1-75 OCHjCHjSOjMe n-Pr 0 CFj 1-76 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 cf ₃ 1-77 OCH ₂ CH ₂ SO ₂ Me Me 1 CFj 1-78 OCH ₂ CH ₂ SO _? Me Et 1 cf ₃ 1-79 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 cf ₃ 1-80 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CFj 1-81 OCH ₂ CH ₂ SO ₂ Me Me 2 CF ₃ 1-82 OCH ₂ CH ₂ SO ₂ Me Et 2 cf ₃ 1-83 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CF _a 1-84 OCH ₂ CH ₂ SQ ₂ Me i-Pr 2 CF ₃

Petition 870180037453, of 05/07/2018, p. 12/36

26/110

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-85 OCOMe Me 0 CF ₃ 1-86 OCOMe Et 0 cf ₃ 1-87 OCOMe n-Pr 0 cf ₃ 1-88 OCOMe i-Pr 0 cf ₃ 1-89 OCOMe Me 1 cf ₃ 1-90 OCOMe Et 1 cf ₃ 1-91 OCOMe n-Pr 1 cf ₃ 1-92 OCOMe i-Pr 1 cf ₃ 193 OCOMe Me 2 cf ₃ 1-94 OCOMe Et 2 cf ₃ 1-95 OCOMe n-Pr 2 cf ₃ 1-96 OCOMe í-Pr Z cf ₃ 1-97 OSOjMe Me 0 cf ₃ 1-98 OSO ₂ Me Et 0 cf ₃ 1-99 OSOjMe n-Pr 0 cf ₃ 1-100 OSO ₂ Me i-Pr 0 CFj 1-101 OSOiMe Me 1 cf ₃ 1-102 OSO ₂ Me Et 1 cf ₃ 1-103 OSO ₃ Me n-Pr 1 CFj 1-104 OSO ₂ Me i-Pr 1 cf ₃ 1-105 OSOjMe Me 2 cf ₃ 1-106 CSO ₂ Me Et 2 cf ₃ 1-107 OSO ₂ Me n-Pr 2 cf ₃ 1-108 OSOjMe i-Pr 2 cf ₃ 1-109 OMe Me 0 here 1-110 OMe Et 0 c ₂ f ₅ 1-111 OMe n-Pr 0 here 1-112 OMe i-Pr 0 c ₂ f ₅ 1-113 OMe Me 1 HERE 1-114 OMe Et 1 HERE 1-115 OMe n-Pr 1 HERE 1-116 OMe i-Pr 1 HERE 1-117 OMe Me 2 c ₂ F ₃

Petition 870180037453, of 05/07/2018, p. 37/128

27/110

Nr. X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-118 OMe Et 2 c ₂ F ₅ 1-119 OMe n-Pr 2 c ₂ f ₅ 1-120 OMe i-Pr 2 c ₂ f ₅ 1-121 OEt Me 0 c ₂ f ₅ 1-122 OEt Et 0 c ₂ f _s 1-123 OEt n-Pr 0 c ₂ f ₅ 1-124 OEt i-Pr 0 c ₂ f ₅ 1-125 OEt Me 1 c ₂ f _s 1-126 OEt Et 1 C ₂ Fs 1-127 OEt n-Pr 1 c ₂ f _s 1-128 OEt i-Pr 1 C ₂ F _s 1-129 OEt Me 2 c ₂ f ₅ 1-130 OEt Et 2 CzF _s 1-131 OEt n-Pr 2 C ₂ F, 1-132 OEt i-Pr 2 c ₂ f ₅ 1-133 0-CHj.c-Rr Me 0 c ₂ f _s 1-134 O-CH ₂ .c-Pr Et 0 C ₂ F _s 1-135 O-CH ₂ c-Pr n-Pr D C ₂ F _s 1-136 O-CH ₂ c-Pr i-Pr 0 c ₂ f ₅ 1-137 O-CH ₂ .c-Rr Me 1 c ₂ f ₅ 1-138 O-CH ₂ .c-Pr Et 1 C ₂ F _s 1-139 O-CH ₂ c-Pr n-Pr 1 C ₂ Fs 1-140 O-CH ₂ .c-Pr i-Pr 1 C ₂ F 5 1-141 O-CH ₂ .C-Pr Me 2 C ₂ F _s 1-142 O-CH ₂ .c-Pr Et 2 c ₂ f _s 1-143 O-CH ₂ .e-Pr n-Pr 2 c ₂ f ₅ 1-144 O-CH ₂ .c-Pr i-Pr 2 C ₂ F _s 1-145 OCH ₂ CH ₂ OMe Me 0 c ₂ f ₅ 1-146 OCH ₂ CH ₂ OMe Et 0 c ₂ f ₅ 1-147 OCH ₂ CH ₂ OMe n-Pr 0 c ₂ f ₅ 1-148 OCH ₂ CH ₂ OMe i-Pr 0 c ₂ f _s 1-149 OCH ₂ CH ₂ OMe Me 1 c _{£ 2} 1-150 OCH ₂ CH ₂ OMe Et 1 c ₂ f ₅

Petition 870180037453, of 05/07/2018, p. 12/38

1/28

Nr. X R ’ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-151 OCH ₂ CH ₂ OMe n-Pr 1 c ₂ f ₅ 1-152 OCH ₂ CH ₂ OMe i-Pr 1 c ₂ f ₅ 1-153 OCHjCHiOMe Me 2 1-154 OCH ₂ CH ₂ OMe Et 2 c ₂ f ₅ 1-155 OCH ₂ CH ₂ OMe n-Pr 2 c ₂ f ₅ 1-156 OCHiCHiOMe i-Pr 2 c ₂ f ₅ 1-157 OCHÍCHíSMe Me 0 c ₂ f _s 1-158 OCHjCHjSMe Et 0 c ₂ f ₅ 1-159 OCH ₂ CH ₂ SMe n-Pr 0 c ₂ f ₅ 1-160 OCH ₂ CH ₂ SMe i-Pr 0 c ₂ f ₅ 1-161 OCH ₂ CH ₂ SMe Me 1 C ₂ F _s 1-162 OCH ₂ CH ₂ SMe Et 1 c ₂ f _s 1-163 OCH ₂ CH ₂ SMe n-Pr 1 C _S F _S 1-164 OCH ₂ CH ₂ SMe i-Pr 1 c ₂ f ₅ 1-165 OCH ₂ CH ₂ SMe Me 2 C ₂ F _s 1-166 OCH ₂ CH ₂ SMe Et 2 c ₂ f ₅ 1-167 OCH ₂ CH ₂ SMe n-Pr 2 c ₂ f ₅ 1-168 OCH ₂ CH ₂ SMe i-Pr 2 c ₂ f ₅ 1-169 OCH ₂ CH ₂ SO ₂ Me Me 0 c ₂ f _s 1-170 OCH ₂ CH ₂ SO ₂ Me Et 0 c ₂ f ₅ 1-171 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 c ₂ f ₅ 1-172 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 c ₂ f ₅ 1-173 OCHjCHÍSOíMe Me 1 c ₂ f _s 1-174 OCH ₂ CH ₂ SO ₂ Me Et 1 C ₂ Fs 1-175 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 c ₂ f ₅ 1-176 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 c ₂ f _s 1-177 OCH ₂ CH ₂ SO ₂ Me Me 2 c ₂ f ₅ 1-178 OCH ₂ CH ₂ SO ₂ Me Et 2 c ₂ f ₅ 1-179 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 c ₂ f _s 1-180 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 c ₂ f ₅ 1-181 OMe Me 0 CCI ₃ 1-182 OMe Et O CCI ₃ 1-183 Who is n-Pr 0 CCI ₃

Petition 870180037453, of 05/07/2018, p. 12/39

1/29

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-184 OMe i-Pr 0 CClj 1-185 OMe Me 1 CCI ₃ 1-186 OMe Et 1 CClj 1-187 OMe n-Pr 1 CClj 1-188 OMe i-Pr 1 CClj 1-189 OMe Me 2 CCI ₃ 1-190 OMe Et 2 CClj 1-191 OMe n-Pr 2 CCI ₃ 1-192 OMe i-Pr 2 CCI ₃ 1-198 OEt Me 0 CClj 1-194 OEt Et 0 CClj 1-195 OEt n-Pr 0 CClj 1-196 OEt i-Pr 0 CClj 1-197 OEt Me 1 CClj 1-198 OEt Et 1 CClj 1-199 OEt n-Pr 1 CClj 1-200 OEt i-Pr 1 CClj 1-201 OEt Me 2 CCI ₃ 1-202 OEt Et 2 CCI ₃ 1-203 OEt n-Pr 2 CClj 1-204 OEt i-Pr 2 CClj 1-205 O-CHj.c-Pr Me 0 CClj 1-206 O-CH ₂ .c-Pr Et 0 CClj 1-207 O-CHi.c-Pr n-Pr 0 CClj 1-208 O-CHi c-Pr i-Pr 0 CClj 1-209 O-CK ₂ .c-Pr Me 1 CClj 1-210 O-CHjX-Pr Et 1 CClj 1-211 0-CHí.c-Pr n-Pr 1 CClj 1-212 O-CH ₂ .c-Pr i-Pr 1 CClj 1-213 O-CH ₂ .c-Pr Me 2 CClj 1-214 O-CH ₂ .c-Pr Et 2 CClj 1-215 O-CH ₂ .c-Pr n-Pr 2 CClj 1-216 O-CH ₂ .c-Pr i-Pr 2 CClj

Petition 870180037453, of 05/07/2018, p. 40/128

1/30

Nr. X R ¹ n y Physical data: ¹ H-NMR: δ [CDCIs] 1-217 OCH ₂ CH ₂ OMe Me 0 CCI ₃ 1-218 OCH ₂ CH ₂ OMe Et 0 CCI ₃ 1-219 OCH ₂ CH ₂ OMe n-Pr 0 CCI ₃ 1-220 OCH ₂ CH ₂ OMe i-Pr 0 CCI ₃ 1-221 OCH ₂ CH ₂ OMe Me 1 CCI ₃ 1-222 OCH ₂ CH ₂ OMe Et 1 CCI ₃ 1-223 OCHaCHjOMe n-Pr 1 CCI ₃ 1-224 OCH ₂ CH ₂ OMe i-Pr 1 CCI ₃ 1-225 OCH ₂ CH ₂ OMe Me 2 CCI ₃ 1-226 OCH ₂ CH ₂ OMe Et 2 CCI ₃ 1-227 OCH ₂ CH ₂ OMe n-Pr 2 CCI ₃ 1-228 OCH ₂ CH ₂ OMe i-Pr 2 CCI ₃ 1-229 OCH ₂ CH ₂ SMe Me 0 CCI ₃ 1-230 OCH ₂ CH ₂ SMe Et 0 CCI ₃ 1-231 OCH ₂ CH ₂ SMe n-Pr 0 CCI ₃ 1-232 OCHiCHiSMe i-Pr 0 ccij 1-233 OCH ₂ CH ₂ SMe Me 1 CCI ₃ 1-234 OCH ₂ CH ₂ SMe Et 1 CCI ₃ 1-235 OCH ₂ CH ₂ SMe n-Pr 1 CCI _S 1-236 OCH ₂ CH ₂ SMe i-Pr 1 CCIj 1-237 OCH ₂ CH ₃ SMe Me 2 CCIj 1-238 OCH ₂ CH ₂ SMe Et 2 CCb 1-239 OCH ₂ CH ₂ SMe n-Pr 2 CCI ₃ 1-240 OCH ₂ CH ₂ SMe i-Pr 2 CCIj 1-241 OCH ₂ CH ₂ SO ₂ Me Me 0 CCIj 1-242 OCH ₂ CH ₂ SO ₂ Me Et 0 CCIj 1-243 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CCIi 1-244 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CCIj 1-245 OCH ₂ CH ₂ SO ₂ IMe Me 1 CCIj 1-246 OCH ₂ CH ₂ SO ₂ Me Et 1 CCIj 1-247 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CCIj 1-243 OCH ₂ CH ₂ SO ₂ IMe i-Pr 1 ccu 1-249 OCH ₂ CH ₂ SO ₂ IMe Me 2 CCI ₃

Petition 870180037453, of 05/07/2018, p. 41/128

1/31

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-250 OCH ₂ CH ₂ SO ₂ Me Et 2 CCI ₃ 1-251 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CCI ₃ 1-252 0CH ₂ CH ₂ SO ₂ Me i-Pr 2 CCI ₃ 1-253 OMe Me 0 chf ₂ 1-254 OMe Et 0 CHF ₂ 1-255 OMe n-Pr 0 CHFj 1-256 OMe í-Pr 0 CHF ₂ 1-257 OMe Me 1 chf ₂ 1-256 OMe Et 1 chf ₂ 1-259 OMe n-Pr 1 chf ₂ 1-260 OMe i-Pr 1 chf ₂ 1-261 OMe Me 2 chf ₂ 1-262 OMe Et 2 chf ₂ 1-263 OMe n-Pr 2 chf ₂ 1-264 OMe i-Pr 2 chf ₂ 1-265 OEt Me 0 chf ₂ 1-266 OEt Et 0 CHFí 1-267 OEt n-Pr 0 CHFj 1-268 OEt i-Pr 0 chf ₂ 1-269 OEt Me 1 CHF ₂ 1-270 OEt Et 1 chf ₂ 1-271 OEt n-Pr 1 chf ₂ 1-272 OEt i-Pr 1 chf ₂ 1-273 OEt Me 2 chf ₂ 1-274 OEt Et 2 chf ₂ 1-275 OEt n-Pr 2 chf ₂ 1-276 OEt i-Pr 2 chf ₂ 1-277 O-CHj-c-Pr Me 0 chf ₂ 1-278 O-CH ₃ -c-Pr Et 0 CHFj 1-279 O - CHj - c-Pr n-Pr 0 chf ₂ 1-280 O - CH ₃ - c-Pr i-Pr 0 chf ₂ 1-281 O - CH ₂ - c-Pr Me 1 chf ₂ 1-282 O-CH ₂ -c-Pr Et 1 chf ₂

Petition 870180037453, of 05/07/2018, p. 42/128

32/110

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-283 0 - CH ₂ - c-Pr n-Pr 1 chf ₂ 1-284 O - CH ₂ - c-Pr i-Pr 1 chf ₂ 1-285 O-CH ₂ -c-Pr Me 2 chf ₂ 1-286 0 - CH ₂ - c-Pr Et 2 chf ₂ 1-287 O - CH _Z - c-Pr n-Rr 2 chf ₂ 1-288 0 - CH ₂ - c-Pr i-Pr 2 CHF _Z 1-289 OCHiCHjOMe Me 0 chf ₂ 1290 OCH ₂ CH ₂ OMe Et 0 chf ₂ 1-291 OCH ₂ CH ₂ OMe n-Pr 0 chf ₂ 1-292 OCH ₂ CH ₂ OMe i-Pr 0 chf ₂ 1-293 OCHjCHjOMe Me 1 chf ₂ 1-294 OCHiCH ₂ OMe El 1 chf ₂ 1-295 OCH ₂ CH ₂ OMe n-Pr 1 chf ₂ 1-296 OCH ₂ CH ₂ OMe i-Pr 1 chf ₂ 1-297 OCH ₃ CH ₂ OMe Me 2 chf ₂ 1-298 OCH ₂ CH ₂ OMe Et 2 chf ₂ 1-299 OCH ₂ CH ₂ OMe n-Pr 2 chf ₂ 1-300 OCH ₂ CHjOMe i-Pr 2 CHFi 1-301 OCH ₂ CH ₂ SMe Me 0 chf ₂ 1-302 OCH ₂ CH ₂ SMe Et 0 chf ₂ 1-303 OCH ₂ CH ₂ SMe n-Pr 0 CHFj 1-304 OCH ₂ CH ₂ SMe i-Pr 0 chf ₂ 1-305 OCH ₂ CH ₂ SMe Me 1 chf ₂ 1-306 OCH ₂ CH ₂ SMe Et 1 chf ₂ 1-307 OCH ₂ CH ₂ SMe n-Pr 1 chf ₂ 1-308 OCH ₂ CH ₂ SMe i-Pr 1 chf ₂ 1-309 OCH ₂ CH ₂ SMe Me 2 chf ₂ 1-310 OCH ₂ CH ₂ SMe Et 2 chf ₂ 1-311 OCH ₂ CH ₂ SMe n-Pr 2 chf ₂ 1-312 OCH ₂ CH ₂ SMe i-Pr 2 chf ₂ 1-313 OCHjCH ₂ S0 ₂ Me Me 0 chf ₂ 1-314 OCH ₂ CH ₂ SO ₂ Me Et 0 chf ₂ 1-315 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 chf ₂

Petition 870180037453, of 05/07/2018, p. 43/128

33/110

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-316 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 chf ₂ 1-317 OCH ₂ CH ₂ SO ₂ Me Me 1 chf ₂ 1-318 OCH ₂ CH ₂ SO ₂ Me Et 1 CHF ₂ 1-319 OCHjCHíSOjMe n-Pr 1 CHFj 1-320 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 chf ₂ 1-321 OCHjCHjSOjMe Me 2 CHF _? 1-322 OCH ₂ CH ₂ SO ₂ Me Et 2 CHFj 1-323 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 chf ₂ 1-32-4 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 chf ₂ 1-325 OMe Me 0 CF (CF ₃ ) ₂ 1-326 OMe Et 0 CF (CF _s ) ₂ 1-327 OMe n-Pr 0 CF (CF ₃ ) ₂ 1-328 OMe i-Pr 0 CF (CF ₃ ) ₂ 1-329 OMe Me 1 CF (CF ₃ ) ₂ 1-330 OMe Et 1 CF (CF ₃ ) ₂ 1-331 OMe n-Pr 1 CF (CF ₃ ) ₂ 1-332 OMe i-Pr 1 CF (CF ₃ ) ₂ 1-333 OMe Me 2 CF {CF _a ) ₂ 1-334 OMe Et 2 CF (CF ₃ ) ₂ 1-335 OMe n-Pr 2 CF {CF ₃ } ₂ 1-336 OMe i-Pr 2 CF {CF ₃ } ₂ 1-337 OEt Me 0 CF (CF ₃ ) ₂ 1-338 OEt Et 0 cf <cf ₃ > ₂ 1-339 OEt n-Pr 0 CF (CF ₃ ) ₂ 1-340 OEt i-Pr 0 CF (CF ₃ ) ₂ 1-341 OEt Me 1 CF {CF ₃ > ₂ 1-342 OEt Et 1 CF (CF ₃ ) ₂ 1-343 OEt n-Pr 1 CF (CF ₃ ) ₂ 1-344 OEt i-Pr 1 CF (CF ₃ ) ₂ 1-345 OEt Me 2 CF (CF ₃ ) ₂ 1-346 OEt Et 2 CF (CF ₃ ) ₂ 1-347 OEt n-Pr 2 CF (CF ₃ ) ₂ 1-348 OEt i-Pr 2 CF (CF ₃ ) ₂

Petition 870180037453, of 05/07/2018, p. 44/128

34/110

Nr, X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-349 0 - CH ₂ - c-Pr Me 0 CF (CF ₃ ) ₂ 1-350 O - CH ₂ - c-Pr Et 0 CF (CF ₃ ) ₂ 1-351 O-CHj-c-Pr n-Pr 0 CF (CF ₃ ) ₃ 1-352 O-CHj-c-Pr i-Pr 0 CF (CF ₃ ) ₂ 1-353 0 - CH ₂ - c-Pr Me 1 CF (CF ₃ ) ₂ 1-354 O-CHj-c-Rr Et 1 CF <CF ₃ ) ₂ 1-355 O-CHi-c-Pr n-Pr 1 CF {CFj) j 1-356 O-CHj-c-Pr i-Pr 1 CF (CF ₃ ) ₂ 1-357 O-CH ₂ -c-Pr Me 2 CF (CF ₃ ) ₂ 1-358 O-CH ₂ -c-Pr Et 2 CF (CF ₃ ) _? 1-359 O-CH ₂ -c-Pr n-Pr 2 CF (CF ₃ ) ₂ 1-360 O-CH ₂ -c-Pr i-Pr 2 CF (CF ₃ ) ₂ 1-361 OCH ₂ CH ₂ OMe Me 0 CF (CF ₃ ) ₂ 1-362 OCHjCHjOMe Et 0 CF (CF ₃ ) ₂ 1-363 OCH ₂ CH ₂ OMe n-Pr 0 CF (CF ₃ ) ₂ 1-364 OCH ₂ CH ₂ OMe t-Pr 0 CF (CF ₃ ) ₃ 1-365 OCHsCHjOMe Me 1 CF (CF ₃ ) ₂ 1-366 OCHjCHjOMe Et 1 CF (CF ₃ ) ₂ 1-367 OCH ₂ CH ₂ OMe n-Pr 1 CF (CF ₃ ) ₂ 1-368 OCH ₂ CH ₂ OMe i-Pr 1 CF (CF ₃ ) ₂ 1-369 OCHjCHjOMe Me 2 CF (CF ₃ ) ₂ 1-370 OCH ₂ CH ₂ ÜMe Et 2 CF (CF ₃ ) ₂ 1-371 OCH ₂ CH ₂ OMe n-Pr 2 CF (CF _} ) ₂ 1-372 OCHjCHjOMe i-Pr 2 CF (CF ₃ ) ₂ 1-373 QCH ₂ CH ₂ SMe Me 0 CF (CF ₃ ) ₂ 1-374 OCh ₂ CH ₂ SMe Et 0 CF (CF ₃ } ₂ 1-375 OCHiCH ₂ SMe n-Pr 0 CF (CF ₃ ) ₂ 1-376 OCH ₂ CH ₂ SMe i-Pr 0 CF (CF ₃ ) ₂ 1-377 OCHiCH ₂ SMe Me 1 CF (CF ₃ > ₂ 1-378 OCHjCHíSMe Et 1 CF (CF ₃ > ₂ 1-379 OCH ₂ CH ₂ SMe n-Pr 1 CF (CF ₃ > ₂ 1-380 OCH ₂ CH ₂ SMe i-Pr 1 CF (CF ₃ > ₂ 1-381 0CH ₂ CH ₂ SMe Me 2 CF (CF ₃ > ₂

Petition 870180037453, of 05/07/2018, p. 45/128

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 1-382 OCH ₂ CH ₂ SMe Et 2 CF (CF ₃ ) ₂ 1-383 OCH ₂ CH ₂ SMe n-Pr 2 CF {CF _a ) ₂ 1-384 OCH ₂ CH ₂ SMe i-Pr 2 CF (CF ₃ ) ₂ 1-385 OCH ₂ CH ₂ SO ₂ Me Me 0 CF (CF ₃ ) ₂ 1-386 OCH ₂ CH ₂ S0 ₂ Me Et 0 CF (CF ₃ ) ₂ 1-387 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CF (CF ₃ ) ₂ 1-388 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 cf <cf ₃ ) ₂ 1-389 0CH ₂ CH ₂ SO ₂ Me Me 1 CF (CF ₃ ) ₂ 1-390 OCH ₂ CH ₂ SO ₂ Me Et 1 CF (CF ₃ ) ₂ 1-391 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CF (CF ₃ ) ₂ 1-392 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CF (CF ₃ ) ₂ 1-393 0CH ₂ CH ₂ SO ₂ Me Me 2 CF (CF ₃ ) ₂ 1-394 OCH ₂ CH ₂ SO ₂ Me Et 2 CF (CF ₃ } ₂ 1-395 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CF (CF ₃ } ₂ 1-396 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CF (CF ₃ ) ₂

Table 2: compounds according to the invention, of the general formula (I), in which R ² means hydroxy, R ³ to R ⁶ mean, respectively, hydrogen, and R ⁷ , as well as R ⁸ mean, respectively, methyl.

SO R ¹ (0

Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 2-1 OH Me α cf ₃ 2-2 OH Et 0 cf ₃ 2-3 OH n-Pr 0 cf ₃ 2-4 OH i-Pr 0 cf ₃

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Nr. X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-5 OH Me 1 cf ₃ 2-6 OH Et 1 CFj 2-7 OH n-Pr 1 cf ₃ 2-8 OH i-Pr 1 cf ₃ 2-9 OH Me 2 cf ₃ 2-10 OH Et 2 cf ₃ 2-11 OH n-Pr 2 cf ₃ 2-12 OH i-Pr 2 cf ₃ 2-13 OMe Me 0 cf ₃ 17.37 / 15.60 (s, 1H), 7.52-7.47 (d / d, 1HJ. 7.23-7.18 (m, 1H), 3 83/3 80 (s, 3H). 279 / 2.47 (t, 2H), 2.42 1 2.41 (s, 3H), 1 93 1.85 <rri, 2H), 1.38 / 1.11 (s, 6H) 2-14 OMe Et 0 cf ₃ 2-15 OMe n-Pr 0 cf ₃ 2-16 OMe i-Pr 0 cf ₃ 2-17 OMe Me 1 cf ₃ 17.12 / 16 33 (5, 1H), 7.58 / 7.55 (d, 1H), 7.50 - 7.42 (m, 1H), 3.86 / 3.84 (s, 3HJ, 3.07 / 3.05 (s, 3H), 2.82 / 2.49 (m, 2H). 1.89 (m, 2H). 1.42 / 1.21 (s, 3H), 1.37 / 1.07 (s, 3H) 2-18 OMe Et 1 cf ₃ 2-19 OMe n-Pr 1 cf ₃ 2-20 OMe i-Pr 1 cf ₃ 2-21 OMe Me 2 cf ₃ 17.13 / 16.39 (s, 1H). 7 73/772 (d. 1H), 7.55 / 7.52 (d, 1H), 3.83 / 3.82 (s, 3H), 3.29 / 3.27 (s, 3H), 2.82 / 2.47 (t, 2H), 1.94-1.87 (m, 2H), 1.41 / 1.12 (3, 6H) 2-22 OMe Et 2 cf ₃ 2-23 OMe n-Pr 2 cf ₃ 2-24 OMe i-Pr 2 CFj 2-25 OEt Me 0 CFj 2-26 OEt Et 0 cf ₃ 2-27 OEt n-Pr 0 CFj 2-28 OEt i-Pr 0 CFj 2-29 OEt Me 1 cf ₃ 2-30 OEt Et 1 cf ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-31 OEt n-Pr 1 CFj 2-32 OEt i-Pr 1 CFj 2-33 OEt Me 2 cf ₃ 2-34 OEt Et 2 CFj 2-35 OEt n-Pr 2 CFj 2-36 OEt i Pr 2 CFj 2-37 O-CHj.c-Pr Me 0 CFj 2-38 O-CH ₂ .c-Pr Et 0 CFj 2-39 O-CH ₂ .c-Pr n-Pr 0 CFj 2-10 O-CH ₂ .c-Pr i-Pr 0 CFj 2-11 0-CH ₂ .c-Pr Me 1 CFj 2-12 O-CH ₂ .c-Pr Et 1 CFj 2-43 O-CH ₂ .c-Pr n-Pr 1 CFj 2-44 O-CH ₂ .c-Pr i-Pr 1 CFj 2-15 O-CH ₂ .c-Pr Me 2 CFj 2-16 O-CH ₂ .c-Rr Et 2 CFj 2-47 O-CH ₂ .c-Rr n-Pr 2 CFj 2-48 O-CHj.c-Pr í-Pr 2 CFj 2-49 OCH ₂ CH ₂ OMe Me 0 CFj 2-50 OCHiCHzOMe Et 0 CFj 2-51 OCH ₂ CH ₂ OMe n-Pr 0 CFj 2-52 OCH ₂ CH ₂ OMe i-Pr 0 CFj 2-53 OCH ₂ CH ₂ OMe Me 1 CFj 2-54 OCH ₂ CH ₂ OMe Et 1 CFj 2-55 OCH ₂ CH ₂ OMe n-Pr 1 CFj 2-56 OCH ₂ CH ₂ OMe t-Pr 1 CFj 2-57 OCH ₂ CH ₂ OMe Me 2 CFj 2-58 OCH ₂ CH ₂ OMe Et 2 CFj 2-59 OCH ₂ CH ₂ OMe n-Pr 2 CFj 2-60 OCH ₂ CH ₂ OMe i-Pr 2 CFj 2-61 OCH ₂ CH ₂ SMe Me 0 CFj 2-62 OCH ₂ CH ₂ SMe Et 0 CFj 2-63 OCH ₂ CH ₂ SMe n-Pr 0 CFj

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-64 OCH ₂ CH ₂ SMe i-Pr 0 cf ₃ 2-65 OCH ₂ CH ₂ SMe Me 1 cf ₃ 2-66 OCH ₂ CH ₂ SMe Et 1 cf ₃ 2-67 OCH _z CH ₂ SMe n-Pr 1 cf ₃ 2-68 OCH ₂ CH ₂ SMe i-Pr 1 cf ₃ 2-69 OCHiCHjSMe Me 2 cf ₃ 2-70 OCH ₂ CH ₂ SMe Et 2 cf ₃ 2-71 OCH ₂ CH ₂ SMe n-Pr 2 CF ₃ 2-72 OCH ₂ CH ₂ SMe i-Pr 2 CF _a 2-73 OCH ₂ CH ₂ SO ₂ Me Me 0 cf ₃ 2-74 OCH ₂ CH ₂ SO ₂ Me Et O cf ₃ 2-75 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 cf ₃ 2-76 OCH ₂ CH ₂ SO ₂ Me t-Pr 0 cf ₃ 2-77 OCH ₂ CH ₂ SO ₂ Me Me 1 cf ₃ 2-78 OCH ₂ CH ₂ SO ₂ Me Et 1 cf ₃ 2-79 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 cf ₃ 2-80 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 cf ₃ 2-81 OCH ₂ CHjSO ₂ Me Me 2 cf ₃ 2-82 OCH ₂ CH ₂ SO ₂ Me Et 2 CFj 2-83 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CF _S 2-84 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CFj 2-85 OCOMe Me 0 CFj 2-86 OCOMe Et 0 CF, 2-87 OCOMe n-Pr 0 CF ₃ 2-88 OCOMe i-Pr 0 CFj 2-89 OCOMe Me 1 cf ₃ 2-90 OCOMe Et 1 cf ₃ 2-91 OCOMe n-Pr 1 cf ₃ 2-92 OCOMe i-Pr 1 cf ₃ 2-93 OCOMe Me 2 cf ₃ 2-94 OCOMe Et 2 cf ₃ 2-95 OCOMe n-Pr 2 cf ₃ 2-96 OCOMe í-Pr 2 cf ₃

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Nr, X R ’ π Y Physical data: ¹ H-NMR: δ [CDCIs] 2-97 0SO ₂ Me Me 0 cf, 2-98 OSOjMe Et 0 cf, 2-99 OSOíMe n-Pr 0 cf. 2-100 OSOjMç i-Pr 0 cf ₃ 2-101 OSOjMe Me 1 cf. 2-102 OSO ^ Ms Et 1 cf, 2-103 OSOgMs n-Pr 1 cf. 2-104 OSOjM & i-Pr 1 CF, 2-105 OSOíMe Me 2 CF, 2-106 OSOjMe Et 2 CF, 2-107 OSOjMe n-Pr 2 CF, 2-106 OSO ₂ Me i-Pr 2 CF, 2-109 OMe Me 0 c, f ₅ 2-110 OMe Et 0 C ₂ F _s 2-111 OMe n-Pr 0 c ₂ f ₅ 2-112 OMe i-Pr 0 c ₂ f ₅ 2-113 OMe Me 1 c ₂ f _s 2-114 OMe Et 1 c ₂ f _s 2-115 OMe n-Pr 1 c ₂ f ₅ 2-116 OMe i-Pr 1 c ₂ f ₅ 2-117 OMe Me 2 c ₂ f ₅ 2-118 OMe Et 2 c ₂ f ₅ 2-119 OMe n-Pr 2 c ₂ f ₅ 2-120 OMe i-Pr 2 c ₂ f ₅ 2-121 OEt Me 0 c ₂ f _s 2-122 OEt Et 0 CjF, 2-123 OEt n-Pr 0 c ₂ F ₅ 2-124 OEt i-Pr 0 c ₂ f, 2-125 OEt Me 1 c, f, 2-126 OEt Et 1 c ₂ f ₅ 2-127 OEt n-Pr 1 c ₂ f ₅ 2-128 OEt i-Pr 1 c ₂ f _s 2-129 OEt Me 2 C ₂ F _s

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 2-130 OEt Et 2 c ₃ f ₅ 2-131 OEt n-Pr 2 CjFj 2-132 OEt i-Pr 2 c ₂ f ₅ 2-133 O-CH ₂ c-Pr Me 0 c ₂ f ₅ 2-134 O-CH ₂ .c-Pr Et 0 Cjfs 2-135 0-CH ₂ c-Pr n-Pr 0 C ₂ F ₅ 2-136 O-CHz.c-Pr i-Pr 0 c ₂ f _s 2-137 O-CHj.c-Pr Me 1 c ₂ f ₅ 2-138 O-ÇH ₂ .c-Pr Et 1 c ₂ f ₅ 2-139 O-CH ₂ .c-Pr n-Pr 1 c ₂ f ₅ 2-140 O-CH ₂ .c-Pr i-Pr 1 c ₂ f ₅ 2-141 0-CH ₂ .c-Pr Me 2 c ₂ f ₅ 2-142 O-CHj.c-Pr Et 2 c ₃ f ₅ 2-143 O-CHj.c-Pr n-Pr 2 c ₂ f ₅ 2-144 O-CHj.c-Pr i-Pr 2 c ₂ f ₅ 2-145 OCH ₂ CH ₂ OMe Me 0 c _s f ₅ 2-146 OCH ₂ CH ₂ OMe Et 0 c ₂ f ₅ 2-147 OCH ₂ CH ₂ OMe n-Pr 0 c ₂ f ₅ 2-148 OCH ₂ CH ₂ OMe i-Pr 0 c ₂ f _s 2-149 OCH ₂ CH ₂ OMe Me 1 c ₂ f _s 2-150 OCH ₂ CH ₃ OMe Et 1 c ₂ f ₅ 2-151 OCH ₃ CH ₃ OMe n-Pr 1 c _{£ 2} 2-152 OCH ₂ CH ₂ OMe i-Pr 1 c ₂ f _s 2-153 OCHjCHjOMe Me 2 c ₂ f _s 2-154 OCH ₂ CH ₂ QMe Et 2 c ₂ f ₅ 2-155 OCH ₂ CH ₂ OMe n-Pr 2 c ₂ f ₅ 2-156 OCH ₃ CH ₂ OMe i-Pr 2 c ₂ f _s 2-157 0CH ₂ CH ₂ SMe Me 0 c ₂ f _s 2-158 OCH ₂ CH ₂ SMe Et 0 c ₂ f ₅ 2-159 OCH ₂ CH ₂ SMe n-Pr 0 c ₂ f ₅ 2-160 OCH ₂ CH ₂ SMe i-Pr 0 c ₂ f _s 2-161 OCH ₂ Cb) ₂ SMe Me 1 c ₂ f ₅ 2-162 OCH ₂ CH ₃ SMe Et 1 c ₂ f ₅

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-163 OCH ₂ CH ₂ SMe n-Rr 1 c ₂ f ₅ 2-164 OCH ₂ CH ₂ SMe i-Pr 1 c ₂ f ₅ 2-165 OCH ₂ CH ₂ SMe Me 2 c ₅ f ₅ 2-166 OCH ₂ CH ₂ SMe Et 2 c ₂ f ₅ 2-167 OCH ₂ CH ₂ SMe n-Pr 2 C ₂ Fs 2-168 OCH ₂ CH ₂ SMe i-Pr 2 c ₂ f _s 2-169 OCH ₂ CH ₂ SO ₂ Me Me 0 c ₂ f ₅ 2-170 OCH ₂ CH ₂ SO ₂ Me Et 0 c ₂ f ₅ 2-171 OCH ₂ CH ₂ SOjMe n-Pr 0 C ₂ Fí 2-172 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 c ₂ f ₅ 2-173 OCHjCHjSOíMe Me 1 C ₂ Fj 2-174 0CH ₂ CH ₂ SO ₂ Me Et 1 c ₂ f ₅ 2-175 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 c ₂ f ₅ 2-176 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 C ₂ F _s 2-177 OCH ₂ CH ₂ SO ₂ Me Me 2 c ₂ f ₅ 2-178 OCH ₂ CH ₂ SO ₂ Me Et 2 c ₂ f _s 2-179 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 c ₂ f ₅ 2-180 OCH ₂ CHjSO ₂ Me i-Pr 2 c ₂ f _s 2-181 OMe Me O CCI ₃ 2-182 OMe Et O CCI ₃ 2-183 OMe n-Pr 0 CCI ₃ 2-184 OMe i-Pr 0 CCI ₃ 2-185 OMe Me 1 CCI ₃ 2-186 OMe Et 1 CCI ₃ 2-187 OMe n-Pr 1 CCI ₃ 2-188 OMe i-Pr 1 CCI ₃ 2-189 OMe Me 2 ccij 2-190 OMe Et 2 CCI ₃ 2-191 OMe n-Pr 2 CCI ₃ 2-192 OMe i-Pr 2 CCI ₃ 2-193 OEt Me 0 CCI ₃ 2-194 OEt Et 0 CCIs 2-195 OEt n-Pr 0 CCI ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-196 OEt i-Pr 0 CCI ₃ 2-197 OEt Me 1 CCI ₃ 2-198 OEt Et 1 CCI ₃ 2-199 OEt n-Pr 1 CCb 2-200 OEt i-Pr 1 CCI ₃ 2-201 OEt Me 2 CCI ₃ 2-202 OEt Et 2 CCI ₃ 2-203 OEt n-Pr 2 CCI ₃ 2-204 OEt i-Pr 2 CCI ₃ 2-205 0-CHj.c-Pr Me 0 CCI ₃ 2-206 0-CH ₂ .oPr Et 0 CCI ₃ 2-207 O-CH ₃ .c-Pr n-Pr 0 CCI ₃ 2-208 O-CH ₂ .c-Pr i-Pr 0 CCI ₃ 2-209 O-CH ₂ .c-Pr Me 1 CCI ₃ 2-210 O-CH ₂ .c-Pr Et 1 CCIa 2-211 O-CH ₂ .c-Pr n-Pr 1 CCI ₃ 2-212 O-CH ₂ .c-Pr i-Pr 1 CCI ₃ 2-213 O-CH ₂ c-Pr Me 2 CCI ₃ 2-214 O-CH ₂ .c-Pr Et 2 CCI ₃ 2-215 O-CH ₂ .c-Pr n-Pr 2 CCI ₃ 2-216 O-CH ₂ .c-Pr i-Pr 2 CCIa 2-217 OCH ₂ CH ₂ OMe Me 0 CCIa 2-218 OCH ₂ CH ₂ OMe Et 0 CCI ₃ 2-219 OCH ₂ CH ₂ OMe n-Pr 0 CCI ₃ 2-220 OCH ₂ CH ₂ OMe í-Pr 0 CCIj 2-221 OCH ₂ CH ₂ OMe Me 1 ccí ₃ 2-222 OCH ₂ CH ₂ OMe Et 1 CC1 ₃ 2-223 OCHjCH ₂ OMe n-Pr 1 ccij 2-224 OCH _: CH ₂ OMe i-Pr 1 CCIa 2-225 OCH ₂ CH ₂ OMe Me 2 CCI ₃ 2-226 ÜCH ₂ CH ₂ OMe Et 2 CCI ₃ 2-227 OCH ₂ CH ₂ OMe n-Pr 2 CCIa 2-228 OCH ₂ CH ₂ OMe i-Pr 2 CCIa

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 2-229 OCH ₂ CH ₂ SMe Me 0 CCI ₃ 2-230 OCH ₂ CH ₂ SMe Et 0 CCI ₃ 2-231 OCH ₂ CH ₂ SMe n-Pr 0 CCI ₃ 2-232 OCHjCHjSMe i-Pr 0 CCIj 2-233 OCH; CH ₂ SMe Me 1 CCIs 2-234 OCHjCHjSMe Et 1 CCIj 2-235 OCH ₂ CH ₂ SMe n-Pr 1 CCb 2-236 OCH ₂ CH ₂ SMe i-Pr 1 CCI ₃ 2-237 OCH ₂ CH ₂ SMe Me 2 CCI ₃ 2-238 OCK ₂ CH ₂ SMe Et 2 CCI ₃ 2-239 OCH ₂ CH ₂ SMe n-Pr 2 CCI ₃ 2-240 OCH _z CH ₂ SMe i-Pr 2 CCI ₃ 2-241 OCH ₂ CH ₂ SO ₂ Me Me 0 CCI ₃ 2-242 OCH ₂ CH ₂ SO ₂ Me Et 0 CCI ₃ 2-243 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CCI ₃ 2-244 OCH ₂ CH ₂ S0 ₂ Me i-Pr 0 CCIi 2-245 OCH ₂ CH ₂ SO ₂ Me Me 1 CCIj 2-246 OCH ₂ CH ₂ SO ₂ Me Et 1 CCIj 2-247 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CCI ₃ 2-248 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CCI ₃ 2-249 OCH ₂ CH ₂ SOjMe Me 2 CCI ₃ 2-250 OCH ₂ CH ₂ SO ₂ Me Et 2 CCI ₃ 2-251 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CCI ₃ 2-252 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 cci ₃ 2-253 OMe Me 0 chf ₂ 2-254 OMe Et 0 chf ₂ 2-255 OMe n-Pr 0 CHFí 2-256 OMe i-Pr 0 chf ₂ 2-257 OMe Me 1 chf ₂ 2-258 OMe Et 1 chf ₂ 2-259 OMe n-Pr 1 chf ₂ 2-260 OMe i-Pr 1 chf ₂ 2-261 OMe Me 2 chf ₂

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Nr, X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-262 OMe Et 2 CHF ₂ 2-263 OMe n-Pr 2 CHFí 2-264 OMe i-Pr 2 chf ₂ 2-265 OEt Me 0 chf ₂ 2-266 OEt Et 0 CHFí 2-267 OEt n-Pr 0 chf ₂ 2-268 OEt i-Pr 0 chf ₂ 2-269 OEt Me 1 chf ₂ 2-270 OEt Et 1 chf ₂ 2-271 OEt n-Pr 1 chf ₂ 2-272 OEt i-Pr 1 chf ₂ 2-273 OEt Me 2 chf ₂ 2-274 OEt Et 2 chf ₂ 2-275 OEt n-Pr 2 chf ₂ 2-276 OEt i-Pr 2 chf ₂ 2-277 O - CHj - c-Pr Me α chf ₂ 2-278 O - CH ₂ - c-Pr Et 0 chf ₂ 2-279 O - CH ₂ - c-Pr n-Pr 0 chf ₂ 2-280 O-CH ₂ -c-Pr i-Pr 0 chf ₂ 2-281 O - CH ₂ - c-Pr Me 1 chf ₂ 2-282 O-CH ₂ -c-Pr Et 1 chf ₂ 2-283 O-CH ₂ -cPr n-Pr 1 chf ₂ 2-284 O-CH ₂ -cPr i-Pr 1 chf ₂ 2-285 O - CH ₂ - c-Pr Me 2 chf ₂ 2-286 O - CH ₂ - c-Pr Et 2 chf ₂ 2-287 O - CH ₂ - c-Pr n-Pr 2 chf ₂ 2-288 O ~ CH ₂ - c-Pr i-Pr 2 chf ₂ 2-289 OCH ₂ CH ₂ OMe Me 0 chf ₂ 2-290 OCH ₂ CH ₂ OMe Et 0 CHFí 2-291 OCH ₂ CH ₂ OMe n-Pr 0 chf ₂ 2-292 OCH ₂ CH ₂ OMe i-Pr 0 chf ₂ 2-293 OCH ₂ CH ₂ OMe Me 1 chf ₂ 2-294 OCH ₂ CH ₂ OMe Et 1 chf ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-295 OCH ₂ CH ₂ OMe n-Pr 1 chf ₂ 2-296 OCH ₂ CH ₂ OMe i-Pr 1 chf ₂ 2-297 OCH ₂ CH ₂ OMe Me 2 chf ₂ 2-298 OCH ₂ CH ₂ OMe Et 2 chf ₂ 2-299 OCH ₂ CH ₂ OMe n-Pr 2 chf ₂ 2-300 OCH ₂ CH ₂ OMe i-Pr 2 chf ₂ 2-301 OCH ₂ CH ₂ SMe Me 0 chf ₂ 2-302 OCH ₂ CH ₂ SMe Et 0 chf ₂ 2-303 OCH ₂ CH ₂ SMe n-Pr 0 chf ₂ 2-304 OCH ₂ CH ₂ SMe i-Pr 0 chf ₂ 2-305 OCH ₂ CH ₂ SMe Me 1 chf ₂ 2-306 OCH ₂ CH ₂ SMe Et 1 chf ₂ 2-307 OCH ₂ CH ₂ SMe n-Pr 1 chf ₂ 2-308 OCH ₂ CH ₂ SMe i-Pr 1 chf ₂ 2-309 OCH ₂ CH ₂ SMe Me 2 chf ₂ 2-3 W OCH ₂ CH ₂ SMe Et 2 chf ₂ 2-311 OCH ₂ CH ₂ SMe n-Pr 2 chf ₂ 2-312 OCH ₂ CH ₂ SMe i-Pr 2 chf ₂ 2-313 OCH ₂ CH ₂ SO ₂ Me Me 0 chf ₂ 2-314 OCH ₂ CH ₂ SO ₂ Me Et 0 chf ₂ 2-315 OCH ₃ CHjSO ₂ Me n-Pr 0 chf ₂ 2-316 OCH ₂ CH2SO ₂ Me i-Pr 0 chf ₂ 2-317 OCH ₂ CHjSO ₂ Me Me 1 chf ₂ 2-318 OCH ₂ CH ₂ SO ₂ Me Et 1 CHF ₂ 2-319 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 chf ₂ 2-320 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CHFj 2-321 OCH ₂ CH ₂ SO ₂ Me Me 2 chf ₂ 2-322 OCH ₂ CH ₅ SO ₂ Me Et 2 chf ₂ 2-323 OCH ₂ CH ₂ SO ₂ Me n-Fr 2 chf ₂ 2-324 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 chf ₂ 2-325 OMe Me 0 CF (CF,) ₂ 2-326 OMe Et 0 CF (CF ₃ ) ₂ 2-327 OMe n-Pr 0 CF (CF ₃ ) ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-328 OMe i-Pr 0 CF (CF ₃ ) ₂ 2-329 OMe Me 1 cf <cf ₃ ) ₃ 2-330 OMe Et 1 cf <cf ₃ ) ₂ 2-331 OMe n-Pr 1 cf <cf ₃ > ₂ 2-332 OMe i-Pr 1 CF (CF ₃ ) ₃ 2-333 OMe Me 2 CF (CF ₃ ) ₂ 2-334 OMe Et 2 CF <CF ₃ ) ₂ 2-335 OMe n-Pr 2 CF (CF ₃ } ₂ 2-336 OMe í-Pr 2 CF (CF ₃ > ₂ 2-337 OEt Me 0 CF (CF ₃ } ₂ 2-338 OEt Et 0 CF (CF ₃ ) ₂ 2-339 OEt n-Pr 0 CF (CF ₃ ) ₂ 2-340 OEt i-Pr 0 CF (CF ₃ ) _z 2-341 OEt Me 1 CF (CF ₃ ) ₂ 2-342 OEt Et 1 CF (CF ₃ ) ₂ 2-343 OEt n-Pr 1 CF (CF ₃ ) ₂ 2-344 OEt i-Pr 1 CF (CF ₃ ) ₂ 2-345 OEt Me 2 CF (CF ₃ ) ₂ 2-346 OEt Et 2 CF (CF ₃ ) ₂ 2-347 OEt n-Pr 2 CF (CF ₃ ) ₂ 2-348 OEt i-Pr 2 CF (CF ₃ ) ₂ 2-349 O - CH ₂ - c-Pr Me 0 CF (CF ₃ ) ₂ 2-350 O - CHj - c-Pr Et 0 CF (CF ₃ ) ₂ 2-351 O - CHj - c-Pr n-Pr 0 CF (CF ₃ ) ₂ 2-352 O - CHj - c-Pr i-Pr 0 CF (CF ₃ ) ₂ 2-353 O - CH ₂ - c-Pr Me 1 CF (CF ₃ ) ₂ 2-354 O - CK ₂ - c-Pr Et 1 CF (CF ₃ ) ₃ 2-355 O-CPj-c-Pr n-Pr 1 CF (CF ₃ ) í 2-356 O - CP ₂ - c-Pr i-Pr 1 CF (CF ₃ ) ₂ 2-357 O - CP ₂ - c-Pr Me 2 CF (CF ₃ ) ₂ 2-358 O - CP ₂ - c-Pr Et 2 CF (CF ₃ ) ₂ 2-359 O - CP ₂ - c-Pr n-Pr 2 CF (CF ₃ ) ₂ 2-360 O - CH ₂ - c-Pr i-Pr 2 CF (CF ₃ ) ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-361 OCH ₂ CH ₂ OMe Me 0 CF (CF ₃ ) ₂ 2-362 OCH ₂ CH ₂ OMe Et 0 CF (CF ₃ ) ₂ 2-363 OCHjCHjOMe n-Pr 0 CF (CF ₃ ) ₂ 2-364 OCH ₂ CH ₂ OMe i-Pjr 0 CF (CF ₃ ) ₂ 2-365 OCH ₂ CH ₂ OMe Me 1 CF (CF ₃ ) ₂ 2-366 OCH ₂ CH ₂ OMe Et 1 CF (CF ₃ ) ₂ 2-367 OCH ₂ CH ₂ OMe n-Pr 1 CF (CF ₃ ) ₂ 2-368 OCH ₂ CH ₂ OMe i-Pr 1 CF (CF ₃ ) j 2-369 OCH ₂ CH ₂ OMe Me 2 CF (CF ₃ ) j 2-370 OCH ₂ CH ₂ OMe Et 2 CF (CF ₃ ) ₂ 2-371 OCH ₂ CH ₂ OMe n-Pr 2 CF (CF ₃ ) ₂ 2-372 OCH ₂ CH ₂ OMe i-Pr 2 CF (CF ₃ ) ₂ 2-373 OCH ₂ CH ₂ SMe Me 0 CF (CF ₃ ) ₂ 2-374 0CH ₂ CH ₂ SMe Et 0 CF (CF ₃ ) ₂ 2-375 OCH ₂ CH ₂ SMe n-Pr 0 CF (CF ₃ ) ₂ 2-376 OCH ₂ CH ₂ SMe i-Pr 0 CF (CF ₃ ) ₂ 2-377 OCH ₂ CH ₂ SMe Me 1 CF (CF ₃ } ₂ 2-378 OCH ₂ CH ₂ SMe Et 1 CF {CF ₃ } ₂ 2-379 OCH ₂ CH ₂ SMe n-Pr 1 CF (CF ₃ ) ₂ 2-380 OCH ₂ CH ₂ SMe i-Pr 1 CF {CF _a ) ₂ 2-381 OCH ₂ CH ₂ SMe Me 2 CF (CF ₃ ) ₂ 2-382 OCH ₂ CH ₂ SMe Et 2 CF (CF ₃ ) ₂ 2-383 OCH ₂ CH ₂ SMe n-Pr 2 CF (CF ₃ ) ₂ 2-384 OCH ₂ CH ₂ SMe i-Pr 2 CF (CF ₃ ) ₂ 2-385 OCH ₂ CH ₂ SO ₂ Me Me 0 CF (CF ₃ ) ₂ 2-386 OCH ₂ CH ₂ SO ₂ Me Et 0 CF (CF ₃ ) ₂ 2-387 OCH ₂ CH ₂ SO _? Me n-Pr 0 CF (CF ₃ ) ₂ 2-388 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CF (CF ₃ ) ₂ 2-389 OCH ₂ CH ₂ SO ₂ Me Me 1 CF (CF ₃ ) ₂ 2-390 OCH ₂ CH ₂ SO ₂ Me Et 1 CF (CFj) ₂ 2-391 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CF (CF ₃ ) ₂ 2-392 OCH ₂ CH _z SO ₂ Me í-Pr 1 CF (CF ₃ ) ₂ 2-393 OCH _z CH ₂ SO ₂ Me Me 2 CF (CF ₃ ) ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 2-394 OCHzCI-LSOíMe Et 2 CF (CF ₃ ) _z 2-395 OCHiCHiSOjMe n-Pr 2 CF (CF ₃ ) ₂ 2-396 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CF (CFj) ₂

Table 3: compounds according to the invention, of the general formula (I), in which R ² stands for hydroxy, R ³ , R ⁴ , R ⁷ and R ⁸ , respectively, hydrogen, and R ⁵ , as well as R ⁶ , mean, respectively, methyl.

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-1 OH Me 0 LL O 3-2 OH Et 0 cf ₃ 3-3 OH n-Pr 0 CFj 3-4 OH i-Pr 0 cf ₃ 3-5 OH Me 1 CFj 3-6 OH Et 1 CFj 3-7 OH n-Pr 1 CFj 3-8 OH i-Pr 1 CFj 3-9 OH Me 2 CFj 3-10 OH Et 2 CFj 3-11 OH n-Pr 2 CFj 3-12 OH i-Pr 2 CFj 3-13 OMe Me 0 CFj 3-14 OMe Et 0 CFj 3-15 OMe n-Pr 0 CFj 3-16 OMe i-Pr 0 CFj 3-17 OMe Me 1 CFj 16.71 (S, 1H), 7.57 (d, 1H). 7 42 (d,

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Nr. X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 1H). 3.87 (s, 3H), 3.07 (s, 3H), 2.71 (0, 1H), 2.64 (d, 1H), 2.38 (d, 1 H) _r 2.24 (d, 1H), 1.17 (s, 3H), 1.11 (s, 3H) 3-18 OMe Et 1 cf ₃ 3-19 OMe n-Pr 1 cf ₃ 3-20 OMe i-Pr 1 cf ₃ 3-21 OMe Me 2 cf ₃ 3-22 OMe Et 2 cf ₃ 3-23 OMe n-Pr 2 cf ₃ 3-24 OMe i-Pr 2 cf ₃ 3-25 OEt Me 0 cf ₃ 3-26 OEt Et 0 cf ₃ 3-27 OEt n-Pr 0 cf ₃ 3-28 OEt i-Pr 0 cf ₃ 3-29 OEt Me 1 cf ₃ 3-30 OEt Et 1 cf ₃ 3-31 OEt n-Pr 1 cf ₃ 3-32 OEt í-Pr 1 CFs 3-33 OEt Me 2 cf ₃ 3-34 OEt Et 2 cf ₃ 3-35 OEt n-Pr 2 cf ₃ 3-36 OEt i-Pr 2 cf ₃ 3-37 O-CH _? .c-Pr Me 0 cf ₃ 3-38 O-CH ₅ c-Pr Et 0 cf ₃ 3-39 O-CHj.c-Pr n-Pr 0 cf ₃ 3-40 O-CH ₂ .c-Pr i-Pr 0 cf ₃ 3-41 O-CHz.c-Pr Me 1 cf ₃ 3-42 O-CH ₂ .c-Pr Et 1 CFj 3-43 O-CH ₂ .c-Pr n-Pr 1 cf ₃ 3-44 O-CH ₂ .c-Pr i-Pr 1 cf ₃ 3-45 O-CH ₂ .c-Pr Me 2 cf ₃ 3-46 O-CH ₂ .c-Pr Et 2 cf ₃ 3-47 O-CH ₂ .c-Pr n-Pr 2 cf ₃ 3-46 O-CH ₂ , c-Pr i-Pr 2 cf ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-49 OCK ₂ CH ₂ OMe Me 0 cf ₃ 3-50 OCH ₂ CH ₃ OMe Et 0 cf ₃ 3-51 OCHzCH ₂ OMe n-Pr 0 cf ₃ 3-52 OCH ₂ CH ₂ OMe i-Pr 0 cf ₃ 3-53 OCH ₂ CH ₂ OMe Me 1 cf ₃ 3-54 OCHzCHjOMe Et 1 cf ₃ 3-55 OCH ₂ CH ₂ OMe n-Pr 1 cf ₃ 3-56 OCH ₂ CH ₂ OMe i-Pr 1 cf ₃ 3-57 OCHiCH ₂ OMe Me 2 cf ₃ 3-58 0CH ₂ CH _z 0Me Et 2 cf ₃ 3-59 OCH ₂ CH ₂ OMe n-Pr 2 cf ₃ 3-60 OCH ₂ CH ₂ OMe i-Pr 2 cf ₃ 3-61 OCHjCHjSMe Me 0 cf ₃ 3-62 OCH ₂ CH ₂ SMe Et 0 cf ₃ 3-63 OCH ₂ CH ₂ SMe n-Pr 0 CFj 3-64 OCH ₂ CH ₂ SMe i-Pr O CFj 3-65 OCH ₂ CH ₂ SMe Me 1 CFj 3-66 OCH ₂ CH ₂ SMe Et 1 cf ₃ 3-67 OCH ₂ CH ₂ SMe n-Pr 1 cf ₃ 3-68 OCH ₂ CH ₂ SMe í-Pr 1 cf ₃ 3-69 OCH ₂ CH ₂ SMe Me 2 cf ₃ 3-70 OCH ₂ CH ₂ SMe Et 2 cf ₃ 3-71 OCH ₂ CH ₂ SMe n-Pr 2 cf ₃ 3-72 OCH ₂ CH ₂ SMe i-Pr 2 cf ₃ 3-73 OCH ₂ CH ₂ SO ₂ Me Me 0 cf ₃ 3-74 OCH ₂ CH _AND SO ₂ Me Et 0 cf ₃ 3-75 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 cf ₃ 3-76 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CFa 3-77 OCH ₂ CH ₂ SO ₂ Me Me 1 CF ₃ 3-78 OCH ₂ CH ₂ SO ₂ Me Et 1 cf ₃ 3-79 OCH ₃ CH ₂ SO ₂ Me n-Pr 1 cf ₃ 3-80 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 cf ₃ 3-81 OCH ₂ CH ₂ SO ₂ Me Me 2 cf ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-82 OCHjCHjSOjMe Et 2 CFs 3-83 OCH ₂ CH ₂ 5O? Me n-Pr 2 CF3 3-34 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CF ₃ 3-85 OCOMe Me 0 CFs 3-86 OCOMe Et 0 CFj 3-87 OCOMe n-Pr 0 CF _S 3-88 OCOMe i-Pr 0 CF ₃ 3-09 OCOMe Me 1 CF ₃ 3-90 OCOMe Et 1 cf ₃ 3-91 OCOMe n-Pr 1 CF ₃ 3-92 OCOMe i-Pr 1 CFs 3-93 OCOMe Me 2 CFs 3-94 OCOMe Et 2 CFs 3-95 OCOMe n-Pr 2 CFs 3-96 OCOMe i-Pr 2 CFs 3-97 OSO2M © Me 0 CFj 3-98 OSO ₂ Me Et 0 CF ₃ 3-99 OSO ₂ Me n-Pr 0 CF ₃ 3-100 OSO ₂ Me i-Pr 0 CFs 3-101 OSO ₅ Me Me 1 CF3 3-102 OSO ₂ Me Et 1 CFs 3-103 OSO ₂ Me n-Pr 1 CFs 3-104 OSO ₂ Me i-Pr 1 CFs 3-105 OSO ₂ Me Me 2 CFs 3-106 OSO ₂ Me Et 2 CF ₃ 3-107 OSO ₂ Me n-Pr 2 CF ₃ 3-108 OSO ₂ Me i-Pr 2 CFs 3-109 OMe Me 0 C ₂ F ₅ 3-110 OMe Et 0 c ₂ f ₅ 3-111 OMe n-Pr 0 c ₃ f ₅ 3-112 OMe i-Pr 0 c ₂ f ₅ 3-113 OMe Me 1 C ₂ F _s 3-114 OMe Et 1 c ₂ f ₅

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 3-115 OMe n-Pr 1 c ₂ f ₅ 3-116 OMe i-Pr 1 C _Z F _S 3-117 OMe Me 2 c ₂ f ₅ 3-118 OMe Et 2 c ₂ f ₅ 3-119 OMe n-Pr 2 c ₂ f _s 3-120 OMe i-Pr 2 c _z f ₅ 3-121 OEt Me 0 c ₂ f ₅ 3-122 OEt Et 0 c ₂ f ₅ 3-123 OEt n-Pr 0 c ₂ f ₅ 3-124 OEt i-Pr 0 c _z f ₅ 3-125 OEt Me 1 c ₂ f _s 3-126 OEt Et 1 c ₂ f ₅ 3-127 OEt n-Pr 1 C _Z F s 3-128 OEt i-Pr 1 c ₂ f ₅ 3-129 OEI Me 2 c ₂ f ₅ 3-130 OEt Et 2 c ₂ f ₅ 3-131 OEt n-Pr 2 c ₂ f ₅ 3-132 OEt i-Pr 2 c ₂ f ₅ 3-133 O-CH ₂ .c-Pr Me 0 c _z f ₅ 3-134 O-CH ₂ c-Pr Et 0 c ₂ f ₆ 3-135 O-CH _z c-Pr n-Pr 0 c ₂ f ₅ 3-136 O-CH ₂ .c-Pr i-Pr 0 c _z f ₅ 3-137 O-CHj.c-Pr Me 1 c _z f ₆ 3-138 O-CH _z c-Pr Et 1 c ₂ f _s 3-139 O-CH ₂ .c-Pr n-Pr 1 C _Z F _È 3-140 O-CHj.c-Pr i-Pr 1 C ₂ F ₆ 3-141 0-CH ₂ .c-Pr Me 2 c ₂ f ₅ 3-142 O-CH ₂ .c-Pr Et 2 C ₂ Fj 3-143 O-CH ₂ .c-Pr n-Rr 2 c ₂ f ₅ 3-144 O-CH _z c-Pr i-Pr 2 c ₂ f ₅ 3-145 OCH ₂ CH ₂ OMe Me 0 c _z f _s 3-146 OCH ₂ CH ₂ OMe Et 0 c ₂ f ₅ 3-147 OCH ₂ CH _z OMe n-Pr 0 c ₂ f ₅

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-148 OCH ₂ CH ₂ OMe i-Pr 0 c ₂ f ₅ 3-149 OCH ₂ CH ₂ OMe Me 1 c ₂ f ₅ 3-150 OCH ₂ CH ₂ OMe Et 1 c ₂ f _s 3-151 OCH ₂ CH ₂ OMe n-Pr 1 c ₅ f ₅ 3-152 OCH ₂ CH ₂ OMe i-Pr 1 c ₂ f ₅ 3-153 OCH ₂ CH ₂ OMe Me 2 c ₂ f ₅ 3-154 OCH ₂ CH ₂ OMe Et 2 c ₂ f ₅ 3-155 OCH ₂ CH ₂ OMe n-Pr 2 c ₂ f _& 3-156 OCH ₂ CH ₂ OMe i-Pr 2 c ₂ f ₅ 3-157 OCH ₂ CH ₂ SMe Me 0 c ₂ f ₅ 3-158 OCH ₂ CH ₂ SMe Et 0 c _{£ 2} 3-159 OCH ₂ CH ₂ SMe n-Pr 0 c ₂ f _s 3-160 OCH ₂ CH ₂ SMe i-Pr 0 c ₂ f ₅ 3-161 OCH ₂ CH ₂ SMe Me 1 c ₂ f ₅ 3-162 OCH ₂ CH ₂ SMe Et 1 c ₂ f ₅ 3-163 OCH ₂ CH ₂ SMe n-Pr 1 c ₂ f ₃ 3-164 OCH ₂ CH ₂ SMe i-Pr 1 c ₂ f ₅ 3-165 OCH ₂ CH ₂ SMe Me 2 c ₂ f ₅ 3-166 OCH ₂ CH ₂ SMe Et 2 c ₂ f ₅ 3-167 OCH ₂ CH ₂ SMe n-Pr 2 c ₂ f ₅ 3-168 OCH ₂ CH ₂ SMe i-Pr 2 c ₂ f ₅ 3-169 OCH ₂ CH _z SO ₂ Me Me 0 c ₂ f ₅ 3-170 OCH ₂ CH ₂ S0 ₂ Me Et 0 c ₂ f _s 3-171 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 c ₂ f ₅ 3-172 OCH _z CH ₂ SO ₂ Me i-Pr 0 c ₂ f ₅ 3-173 OCH ₂ CH ₂ SO ₂ Me Me 1 c ₂ f ₅ 3-174 OCH ₂ CH ₂ SO _z Me Et 1 c ₂ f ₅ 3-175 OCH ₂ CH ₂ S0 ₂ Me n-Pr 1 c ₂ f ₅ 3-176 OCH ₂ CH ₂ S0 ₂ Me i-Pr 1 c ₂ f ₃ 3-177 OCH ₂ CHjS0 ₂ Me Me 2 c ₂ f _s 3-178 OCH ₂ CH ₂ SO ₂ Me Et 2 c ₂ f ₅ 3-179 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 c ₂ f ₅ 3-180 OCH ₂ CH _z SO ₂ Me i-Pr 2 c ₂ f _s

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 3-1S1 OMe Me 0 CCIj 3-182 OMe Et 0 CCI ₃ 3-183 OMe n-Pr 0 CCIj 3-184 OMe i-Pr 0 CCI ₃ 3-185 OMe Me 1 CCI, 3-186 OMe Et 1 CCI, 3-187 ◦Me n-Pr 1 CCIj 3-188 OMe i-Pr 1 CCI ₃ 3-189 OMe Me 2 CCIj 3-190 OMe Et 2 CCI, 3-191 OMe n-Pr 2 CCI ₃ 3-192 OMe i-Pr 2 CCI ₃ 3-193 OEt Me 0 CCI ₃ 3-194 OEt Et 0 CCI ₃ 3-195 OEt n-Pr 0 CCI, 3-196 OEt i-Pr 0 CCI ₃ 3-197 OEt Me 1 CCI ₃ 3-198 OEt Et 1 CCIj 3-199 OEt n-Pr 1 CCIj 3-200 OEt i-Pr 1 CCI ₃ 3-201 OEt Me 2 CCIj 3-202 OEt Et 2 CCIj 3-203 OEt n-Pr 2 CCIj 3-204 OEt i-Pr 2 CCIj 3-205 O-CH ₂ c-Pr Me 0 CCIj 3-206 O-CH ₂ _c-Pr Et 0 CCI ₃ 3-207 O-CH ₂ .c-Pr n-Pr 0 CCIj 3-206 O-CH ₂ .c-Pr i-Pr 0 CCIj 3-209 O-CH ₂ .c-Pr Me 1 CCI ₃ 3-210 O-CH ₂ .c-Pr Et 1 CCIj 3-211 O-CH ₂ .c-Pr n-Pr 1 CCIj 3-212 O-CH ₂ .c-Pr i-Pr 1 CCIj 3-213 O-CH ₂ .c-Pr Me 2 CCIj

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Nr, X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-214 O-CH ₂ .c-Pr Et 2 CCI ₃ 3-215 O-CHí.c-Pr n-Pr 2 cci ₃ 3-216 O-CH ₂ .c-Pr i-Pr 2 CCI ₃ 3-217 OCH ₂ CH ₂ OMe Me 0 CCI ₃ 3-218 OCHiCHiOMe Et 0 cci ₃ 3-219 OCH ₂ CH ₂ OMe n-Pr 0 CCI ₃ 3-220 OCH ₂ CH ₂ OMe i-Pr 0 CCI ₃ 3-221 OCH ₂ CH ₂ OMe Me 1 CCI ₃ 3-222 OCH ₂ CH ₂ OMe Et 1 CCI ₃ 3-223 OCH ₂ CH ₂ OMe n-Pr 1 CCI ₃ 3-224 OCH ₂ CH ₂ OMe i-Pr 1 CCI ₃ 3-225 OCH ₂ CH ₂ OMe Me 2 CCI ₃ 3-226 OCH ₂ CH ₂ OMe Et 2 CCI ₃ 3-227 OCH ₂ CH ₂ OMe n-Pr 2 CCI ₃ 3-228 OCHjCHaOMe i-Pr 2 CCI ₃ 3-229 OCH ₂ CH ₂ SMe Me 0 CCI ₃ 3-230 OCH ₂ CH ₂ SMe Et 0 CCI ₃ 3-231 OCH ₂ CH ₂ SMe n-Pr 0 CCI ₃ 3-232 OCH ₂ CH ₂ SMe i-Pr 0 CCI ₃ 3-233 OCH ₂ CH ₂ SMe Me 1 CCI ₃ 3-234 OCH ₂ CH ₂ SMe Et 1 CCIj 3-235 OCH ₂ CH ₂ SMe n-Pr 1 CCI ₃ 3-236 OCH ₂ CH ₂ SMe i-Pr 1 CCI ₃ 3-237 OCH ₂ CH ₂ SMe Me 2 CCI ₃ 3-238 OCH ₂ CH ₂ SMe Et 2 CCI ₃ 3-239 OCH ₂ CH ₂ SMe n-Pr 2 CCI ₃ 3-240 OCH ₂ CH ₂ SMe i-Pr 2 CCI ₃ 3-241 OCH ₂ CH ₂ SO ₂ Me Me 0 CCI ₃ 3-242 OCH ₂ CH ₂ SO ₂ Me Et 0 CCI ₃ 3-243 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CCI ₃ 3-244 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CCI ₃ 3-245 OCH ₂ CH ₂ SO ₂ Me Me 1 CCI ₃ 3-246 OCH ₂ CH ₂ SO ₂ Me Et 1 CCI ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-247 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CCI ₃ 3-248 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CCÍ ₃ 3-249 OCH ₂ CH ₂ S0 ₂ Me Me 2 CCIj 3-250 OCH ₂ CH ₂ SO ₂ Me Et 2 CCI ₃ 3-251 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CCI ₃ 3-252 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CCI ₃ 3-253 OMe Me 0 chf ₂ 3-254 OMe Et 0 chf ₂ 3-255 OMe n-Pr 0 chf ₂ 3-256 OMe i-Pr 0 chf ₂ 3-257 OMe Me 1 chf ₂ 3-258 OMe Et 1 chf ₂ 3-259 OMe n-Pr 1 chf ₂ 3-260 OMe i-Pr 1 CHFj 3-261 OMe Me 2 CHFj 3-262 OMe Et 2 CHFà 3-263 OMe n-Pr 2 chf ₂ 3-264 OMe i-Pr 2 chf ₂ 3-265 OEt Me 0 chf ₂ 3-266 OEt Et 0 chf ₂ 3-267 OEt n-Pr 0 chf ₂ 3-268 OEt i-Pr 0 CHF _a 3-269 OEt Me 1 chf ₂ 3-270 OEt Et 1 chf ₂ 3-271 OEt n-Pr 1 chf ₃ 3-272 OEt i-Pr 1 chf ₂ 3-273 OEt Me 2 chf ₂ 3-274 OEt Et 2 chf ₂ 3-275 OEt n-Pr 2 chf ₂ 3-276 OEt i-Pr 2 chf ₂ 3-277 O - CH ₂ - c-Pr Me 0 chf ₂ 3-278 O - CH ₂ - c-Pr Et 0 chf ₂ 3-279 O-CH ₂ -c-Pr n-Pr 0 chf ₂

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 3-280 O-CH ₂ -c-Pr í-Pr 0 chf ₂ 3-281 0 —CH ₂ -c-Pr Me 1 chf ₂ 3-282 O-CHj-c-Pr Et 1 chf ₂ 3-283 O-CH ₂ -c-Pr n-Pr 1 chf ₂ 3-284 0 —CH ₂ -c-Pr Í-Pr 1 chf ₂ 3-285 O-CHz-c-Pr Me 2 CHFj 3-286 O - CH ₂ - c-Pr Et 2 chf ₂ 3-287 O - CH ₂ - c-Pr n-Pr 2 chf ₂ 3-288 O - CH ₂ - c-Pr i-Pr 2 chf ₂ 3-289 OCH ₂ CH ₂ OMe Me 0 chf ₂ 3-290 OCH ₂ CH ₂ OMe Et 0 chf ₂ 3-291 OCH ₂ CK ₂ OMe n-Pr 0 chf ₂ 3-292 OCH _z CH ₂ OMe i-Pr 0 chf ₂ 3-293 OCH ₂ CH ₂ OMe Me 1 chf ₂ 3-294 OCH ₂ CH ₂ OMe Et 1 chf ₂ 3-295 OCH ₂ CH ₂ OMe n-Pr 1 chf ₂ 3-296 OCH ₂ CH ₂ OMe i-Pr 1 chf ₂ 3-297 OCH ₂ CH ₂ OMe Me 2 chf ₂ 3-298 OCH ₂ CH ₂ OMe Et 2 CHF; 3-299 OCH ₂ CH ₂ OMe n-Pr 2 chf ₂ 3-300 OCH ₂ CH ₂ OMe i-Pr 2 chf ₂ 3-301 OCH ₂ CH ₂ SMe Me 0 chf ₂ 3-302 OCH ₂ CH ₂ SMe Et 0 cpf ₂ 3-303 OCH ₂ CH ₂ SMe n-Pr 0 chf ₂ 3-304 OCH ₂ CH ₂ SMe i-Pr 0 chf ₂ 3-305 OCH ₂ CH ₂ SMe Me 1 cpf ₂ 3-306 OCH ₂ CH ₂ SMe Et 1 chf ₂ 3-307 OCH _to CH _to SMe n-Pr 1 chf ₂ 3-308 OCH ₂ CH ₂ SMe i-Pr 1 chf ₂ 3-309 OCH ₂ CH ₂ SMe Me 2 chf ₂ 3-310 OCH _to CH _to SMe Et 2 cpf ₂ 3-311 OCH ₂ CH ₂ SMe n-Pr 2 chf ₂ 3-312 OCH ₂ CH ₂ SMe i-Pr 2 chf ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-313 OCH ₂ CH ₂ SO _z Me Me 0 chf ₂ 3-314 OCH _z CH ₂ SO ₂ Me Et 0 chf ₂ 3-315 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 chf ₂ 3-316 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 chf ₂ 3-317 OCH ₂ CH ₂ SO ₂ Me Me 1 chf ₂ 3-318 OCH ₂ CH ₂ SO ₂ Me Et 1 chf ₂ 3-319 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 chf ₂ 3-320 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 chf ₂ 3-321 OCH ₂ CH ₂ SO ₂ Me Me 2 chf ₂ 3-322 OCH ₂ CH ₂ SO ₂ Me Et 2 chf ₂ 3-323 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 chf ₂ 3-324 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 chf ₂ 3-325 OMe Me 0 CF (CFj) ₂ 3-326 OMe Et 0 CF (CF ₃ ) ₂ 3-327 OMe n-Pr 0 CF (CFj) ₂ 3-328 OMe i-Pr 0 CF (CF ₃ ) ₂ 3-329 OMe Me 1 CF (CF ₃ ) ₂ 3-330 OMe Et 1 CF (CF ₃ ) _z 3-331 OMe n-Pr 1 CF (CF ₃ ) ₂ 3-332 OMe i-Pr 1 CF (CF ₃ ) ₂ 3-333 OMe Me 2 CF (CF ₃ ) ₂ 3-334 OMe Et 2 CF (CF ₃ ) ₂ 3-335 OMe n-Pr 2 CF (CF ₃ ) ₂ 3-335 OMe i-Pr 2 CF (CF ₃ } ₂ 3-337 OEt Me 0 CF (CF ₃ ) ₂ 3-338 OEt Et 0 CF <CF ₃ } ₂ 3-339 OEt n-Pr 0 CF (CF _a ) í 3-340 OEt i-Pr 0 CF (CF ₃ ) ₂ 3-341 OEt Me 1 CF (CF ₃ ) ₂ 3-342 OEt Et 1 CF (CF ₃ ) ₂ 3-343 OEt n-Pr 1 CF (CF ₃ ) ₂ 3-344 OEt i-Pr 1 CF (CF ₃ ) ₂ 3-345 OEt Me 2 CF (CF ₃ ) _z

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Nr, X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-346 OEt Et 2 CF (CFj) ₂ 3-347 OEt n-Pr 2 cf <cf ₃ ) ₂ 3-348 OEt i-Pr 2 CF (CF ₃ } ₂ 3-349 O-CH ₂ -c-Pr Me 0 CF (CF ₃ ) ₂ 3-350 O-CH ₂ -c-Pr Et 0 cf <cf ₃ > ₂ 3-351 O-CHj-c-Pr n-Pr 0 CF (CFj} ₂ 3-352 O-CH ₂ -c-Pr i-Pr 0 CF (CF ₃ } ₂ 3-353 O-CH ₂ -c-Pr Me 1 CF (CF ₃ > ₂ 3-354 O -CH ₂ -c-Pr Et 1 CF (CF ₃ > ₂ 3-355 O-CH ₂ -c-Pr n-Pr 1 CF (CF ₃ } ₂ 3-356 O-CH ₂ -c-Pr i-Pr 1 CF (CF ₃ } ₂ 3-357 O - CH ₂ —c-Pr Me 2 CF (CF ₃ } ₂ 3-358 O-CH ₂ -c-Pr Et 2 CF (CF ₃ ) ₂ 3-359 O - CHj - c-Pr n-Pr 2 CF (CF ₃ ) ₂ 3-360 O - CH ₂ - c-Pr i-Pr 2 CF (CF ₃ ) ₂ 3-361 OCH ₂ CH ₂ OMe Me 0 CF (CF ₃ ) ₂ 3-362 OCH ₂ CH ₂ OMe Et 0 CF (CF ₃ ) ₂ 3-363 OCH ₂ CH ₂ OMe n-Pr 0 CF (CF ₃ ) ₂ 3-364 OCH ₂ CH ₂ OMe i-Pr 0 CF <CF ₃ ) _s 3-365 OCH ₂ CH ₂ OMe Me 1 CF (CFj) ₂ 3-366 OCH ₂ CH ₂ OMe Et 1 CF (CF ₃ ) ₂ 3-367 OCH ₂ CH ₂ OMe n-Pr 1 CF (CF ₃ ) ₂ 3-368 OCH ₂ CH ₂ OMe i-Pr 1 CF (CFj) ₂ 3-369 OCHjCHjOMe Me 2 CF (CF ₃ ) ₂ 3-370 GCH ₂ CH ₂ OMe Et 2 CF (CFj) ₂ 3-371 OCH ₂ CH ₂ OMe n-Pr 2 CF (CFj) ₂ 3-372 OCH ₂ CH ₂ OMe i-Pr 2 CF (CFj) ₂ 3-373 OCH ₂ CH ₂ SMe Me 0 CF (CF _a ) ₂ 3-374 OCH ₂ CH ₂ SMe Et 0 CF (CFj) ₂ 3-375 OCH ₂ CH ₂ SMe n-Pr 0 CF (CFj) ₂ 3-376 OCH ₂ CH ₂ SMe i-Pr 0 CF (CFj) ₂ 3-377 OCH ₂ CH ₂ SMe Me 1 CF (CFj) ₂ 3-378 OCH ₂ CH ₂ SMe Et 1 CF (CF ₃ ) ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 3-379 OCH ₂ CH ₂ SMe n-Pr 1 CF (CFj) ₂ 3-380 OCH ₂ CH ₂ SMe i-Pr 1 CF (CF ₃ ) ₂ 3-381 OCH ₂ CH ₂ SMe Me 2 CF (CF ₃ ) ₂ 3-382 OCH ₂ CH ₂ SMe Et 2 CF (CF ₃ ) ₂ 3-383 OCH ₂ CH ₂ SMe n-Pr 2 CF (CF ₃ ) ₂ 3-384 OCH ₂ CH ₂ SMe i-Pr 2 CF (CF ₃ ) ₂ 3-385 OCH ₂ CH ₂ SO ₂ Me Me 0 CF (CF ₃ ) ₂ 3-386 OCH _z CH ₂ SO ₃ Me Et 0 CF (CF ₃ ) ₂ 3-387 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CF (CF ₃ ) ₂ 3-388 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CF (CF ₃ ) ₂ 3-389 OCH ₂ CH ₂ SO ₂ Me Me 1 CF (CF ₃ ) ₂ 3-390 OCH ₂ CH ₂ SO ₂ Me Et 1 CF (CFj) ₂ 3-391 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CF (CF ₃ ) ₂ 3-392 OCH ₂ CH ₂ SO ₂ Me i-Rr 1 CF (CFj) ₂ 3-393 OCH ₂ CH ₂ SO ₂ Me Me 2 CF (CFj) ₂ 3-394 OCH ₂ CH ₂ SO ₂ Me Et 2 CF (CF ₃ ) ₂ 3-395 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CF <CFj) ₂ 3-396 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CF (CF ₃ > ₂

Table 4: compounds according to the invention, of the general formula (I), in which R ² means hydroxy, R ³ , R ⁴ , R ⁵ , R ⁷ and R ⁸ respectively mean hydrogen, as R ⁶ means, respectively, methyl.

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-1 OH Me 0 cf ₃ 4-2 OH Et 0 cf ₃ 4-3 OH n-Pr O cf ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-4 OH í-Pr 0 CF, 4-5 OH Me 1 cf ₃ 4-6 OH Et 1 cf, 4-7 OH n-Pr 1 cf ₃ 4-8 OH i-Pr 1 cf ₃ 4-9 OH Me 2 cf ₃ 4-10 OH Et 2 cf ₃ 4-11 OH n-Pr 2 cf, 4-12 OH i-Pr 2 cf, 4-13 OMe Me 0 cf ₃ 16.88 (S. 1H). 7.4B (d, 1H), 7 17 (d. 1H), 3.83 (s, 3H), 2.81 (m, 1H), 2.53 2.45 (m, 2H), 2.42 (s, 3H), 2 31 (m, 1H), 2.13 (dd, 1H), 1.13 (d, 3H) 4-14 OMe Et 0 cf ₃ 4-15 OMe n-Pr 0 cf ₃ 4-16 OMe i-Pr 0 cf ₃ 4-17 OMe Me 1 cf ₃ 16.68 /16.57 (s, 1H), 7.54 (d. 1H), 7.41 {d ί d, 1H), 3.86 (s / s, 3H), 3.06 (s / s, 3H), 2.84 (m, 1H), 2.60 - 2.04 (m, 4H), 1.13 (m, 3H) 4-1Θ OMe Et 1 cf ₃ 4-19 OMe n-Pr 1 CF, 4-20 OMe i-Pr 1 CF, 4-21 OMe Me 2 CF, 16.61 (s, 1H), 7.71 (d, 1H), 7.50 (d, 1 Η), 3.S3 (s, 3H). 3.30 <s, 3H) _r 2.85 (m, 1H), 2.56 - 2.46 (m, 2H], 2.32 (m, 1H), 2.15 (dd, 1H), 1.13 (d. 3H} 4-22 OMe Et 2 cf ₃ 4-23 OMe n-Pr 2 cf ₃ 4-24 OMe i-Pr 2 CF _a 4-25 OEt Me 0 cf ₃ 4-26 OEt Et 0 cf ₃ 4-27 OEt n-Pr 0 cf ₃ 4-28 OEt i-Pr 0 cf ₃ 4-29 OEt Me 1 CF,

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 4-30 OEt Et 1 cf ₃ 4-31 OEt n-Pr 1 CFj 4-32 OEt i-Pr 1 CFj 4-33 OEt Me 2 CFj 4-34 OEt Et 2 CFj 4-35 OEt n-Pr 2 CFj 4-36 OEt i-Pr 2 CFj 4-37 O-CH ₂ -c-Pr Me 0 CFj 4-38 O-CH ₂ -c-Pr Et 0 CFj 4-39 O - CH ₂ - c-Pr n-Pr 0 CFj 4-40 O - CH ₂ - c-Pr i-Pr 0 CFj 4-11 O - CH ₂ - c-Pr Me 1 CFj 4-42 O - CH ₂ - c-Pr Et 1 CFj 4-43 O - CH ₂ - c-Pr n-Pr 1 CFj 4-44 The —CH ₂ -c-Pr í-Pr 1 CFj 4-45 O-CH ₂ -c-Pr Me 2 CFj 4-46 O - CH ₂ - c-Pr Et 2 CFj 4-47 O - CH ₂ - c-Pr n-Pr 2 CFj 4-48 O - CH ₂ - c-Pr i-Pr 2 CFj 4-49 OCH ₂ CH ₂ OMe Me 0 CFj 4-50 OCH ₂ CH ₂ OMe Et 0 CFj 4-51 OCH ₂ CH ₂ OMe n-Pr 0 CFj 4-52 OCH ₂ CH ₂ OMe i-Pr 0 CFj 4-53 OCH ₂ CH ₂ GMe Me 1 CFj 4-54 OCH ₂ CH ₂ OMe Et 1 CFj 4-55 OCH ₂ CH ₂ OMe n-Pr 1 CFj 4-56 OCH ₂ CH ₂ OMe i-Pr 1 CFj 4-57 OCH ₂ CH ₂ OMe Me 2 CFj 4-58 OCH ₂ CH ₂ OMe Et 2 CFj 4-59 OCH ₂ CH ₂ OMe n-Pr 2 CFj 4-60 OCH ₂ CH ₂ OMe i-Pr 2 CFj

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-61 OCH ₂ CH ₂ SMe Me O cf ₃ 4-62 OCH ₂ CH ₂ SMe Et O cf ₃ 4-63 OCH ₂ CH ₂ SMe n-Pr 0 cf ₃ 4-64 OCH ₂ CH ₂ SMe i-Pr 0 cf ₃ 4-65 OCH ₂ CH ₂ SMe Me 1 cf ₃ 4-66 OCH ₂ CH ₂ SMe Et 1 cf ₃ 4-67 OCH ₂ CH ₂ SMe n-Pr 1 cf ₃ 4-68 OCH ₃ CH ₂ SMe i-Pr 1 cf ₃ 4-69 OCH ₂ CH ₂ SMe Me 2 cf ₃ 4-70 OCH ₂ CH ₂ SMe Et 2 cf ₃ 4-71 OCH ₂ CH ₂ SMe n-Pr 2 cf ₃ 4-72 OCH ₂ CH ₂ SMe i-Pr 2 cf ₃ 4-73 OCH ₂ CH ₂ SO ₂ Me Me D cf ₃ 4-74 OCH ₂ CH ₂ SO ₂ Me Et 0 cf ₃ 4-75 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 cf ₃ 4-76 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 cf ₃ 4-77 OCH ₂ CH ₂ SO ₂ Me Me 1 cf ₃ 4-78 OCH ₂ CH ₂ SO ₂ Me Et 1 cf ₃ 4-79 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 cf ₃ 4-80 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 cf ₃ 4-81 OCH ₂ CH ₂ SO ₂ Me Me 2 cf ₃ 4-82 OCH ₂ CH ₂ SO ₂ Me Et 2 CFj 4-83 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 cf ₃ 4-84 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 cf ₃ 4-85 OCOMe Me O cf ₃ 4-86 OCOMe Et 0 cf ₃ 4-87 OCOMe n-Pr 0 cf ₃ 4-88 OCOMe i-Pr 0 cf ₃ 4-89 OCOMe Me 1 cf ₃ 4-90 OCOMe Et 1 cf ₃ 4-91 OCOMe n-Pr 1 cf ₃

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 4-92 OCOMe i-Pr 1 CFs 4-93 OCOMe Me 2 CF ₃ 4-94 OCOMe Et 2 cf ₃ 4-95 OCOMe n-Pr 2 cf ₃ 4-96 OCOMe i-Pr 2 cf ₃ 4-97 OSO ₂ Me Me 0 cf ₃ 4-98 OSOjMe Et 0 cf ₃ 4-99 OSÚjMe n-Pr 0 cf ₃ 4-100 OSOjMe i-Pr 0 cf ₃ 4-101 OSOíMe Me 1 CF ₃ 4-102 OSO ₂ Me Et 1 cf ₃ 4-103 OSO ₂ Me n-Pr 1 CFs 4-104 OSO ₂ Me i-Pr 1 CFs 4-105 OSOjMe Me 2 CF ₃ 4-106 OSO ₂ Me Et 2 CFs 4-107 OSO ₂ Me n-Pr 2 CFs 4-108 OSO ₂ Me i-Pr 2 CFs 4-109 OMe Me 0 c ₂ f ₅ 4-110 OMe Et 0 c ₂ f ₅ 4-111 OMe n-Pr 0 c ₂ f ₅ 4-112 OMe i-Pr 0 c ₂ f ₅ 4-113 OMe Me 1 c ₂ f ₃ 4-114 OMe Et 1 c ₂ f ₅ 4-115 OMe n-Pr 1 c ₂ f ₅ 4-116 OMe i-Pr 1 c ₂ f _s 4-117 OMe Me 2 c ₂ f ₅ 4-11B OMe Et 2 c ₂ f ₅ 4-119 OMe n-Pr 2 c ₂ f ₅ 4-120 OMe í-Pr 2 c ₂ f ₅ 4-121 OEt Me 0 C ₂ F _s 4-122 OEt Et 0 c ₂ f ₅

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 4-123 OEt n-Pr 0 CjF _s 4-124 OEt i-Pr 0 c ₂ f ₅ 4-125 OEt Me 1 c ₂ f ₅ 4-126 OEt Et 1 c ₂ f ₅ 4-127 OEt n-Pr 1 c ₂ f ₅ 4-128 OEt i-Pr 1 c ₃ f ₃ 4-129 OEt Me 2 c ₂ f _s 4-130 OEt Et 2 c ₂ f ₅ 4-131 OEt n-Pr 2 c ₂ f ₅ 4-132 OEt i-Pr 2 c ₂ f ₅ 4-133 OCHj-c-Pr Me 0 c ₂ f _s 4-134 OCH ₂ -c-Pr Et 0 c ₂ f ₅ 4-135 OCH ₂ -c-Pr n-Pr 0 c ₂ f ₅ 4-136 OCH ₂ -c-Pr i-Pr 0 c ₂ f ₅ 4-137 OCH ₂ -c-Pr Me 1 c ₂ f ₅ 4-138 OCHí-c-Pr Et 1 c ₂ f _s 4-139 OCHí-c-Pr n-Pr 1 c ₂ f ₃ 4-140 OCH ₂ -c-Pr i-Pr 1 c ₂ f ₅ 4-141 OCH ₂ -c-Pr Me 2 c ₂ f _s 4-142 OCHz-c-Pr Et 2 c ₂ f ₅ 4-143 OCH.-c-Pr n-Pr 2 C _Z F _S 4-144 OCHi-c-Pr i-Pr 2 c ₂ F ₅ 4-145 OCH ₂ CH ₂ OMe Me 0 c ₂ f ₅ 4-146 OCH ₂ CH ₂ OMe Et 0 c ₂ f ₅ 4-147 OCH ₂ CH ₂ OMe n-Pr 0 c ₂ f ₅ 4-148 OCH ₂ CH ₂ OMe i-Pr 0 C ₂ F _s 4-149 OCH ₂ CH ₂ OMe Me 1 CzF, 4-150 OCH ₂ CH ₂ OMe Et 1 c ₂ f ₅ 4-151 OCH ₂ CH ₂ OMe n-Pr 1 c ₂ f ₅ 4-152 OCH ₂ CH ₂ OMe i-Pr 1 c ₂ f ₅ 4-153 OCH ₂ CH ₂ OMe Me 2 c ₂ f ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-154 OCH ₂ CH ₂ OMe Et 2 c ₂ f ₅ 4-155 OCH ₂ CH ₂ OMe n-Pr 2 c ₂ f _s 4-156 OCH _z CH ₂ OMe i-Pr 2 c ₂ f _s 4-157 OCHzCHzSMe Me 0 c ₂ f ₅ 4-158 OCH ₂ CH ₂ SMe Et 0 c ₂ f ₅ 4-159 OCH ₂ CH ₂ SMe n-Pr 0 c ₂ f _s 4-160 OCH ₂ CH ₂ SMe i-Pr 0 c ₂ f _s 4-161 OCH ₂ CH ₂ SMe Me 1 C ₂ F; 4-162 OCH ₂ CH ₂ SMe Et 1 c ₂ f ₅ 4-163 OCH ₂ CH ₂ SMe n-Pr 1 c ₂ f _s 4-164 OCH ₂ CH ₂ SMe i-Pr 1 c ₂ f ₅ 4-165 OCH ₂ CH ₂ SMe Me 2 c ₂ f ₅ 4-166 OCH ₂ CH ₂ SMe Et 2 c ₂ f ₅ 4-167 OCHÍCHíSMe n-Pr 2 c ₂ f ₅ 4-168 OCH ₂ CH ₂ SMe i-Pr 2 c ₂ f ₅ 4-169 OCH ₂ CH ₂ SO ₂ Me Me 0 c ₂ f ₅ 4-170 OCH ₂ CH ₂ SO ₂ Me Et 0 c ₂ f ₅ 4-171 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 c ₂ f ₅ 4-172 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 c ₂ f ₅ 4-173 OCH ₂ CH ₂ SO ₂ Me Me 1 c ₂ f. 4-174 OCH ₂ CH ₂ SO ₂ Me Et 1 c ₂ f ₅ 4-175 OCH ₂ CH; SO ₂ Me n-Pr 1 c ₂ f ₅ 4-176 OCH ₂ CH ₂ SG ₂ Me i-Pr 1 C ₂ F a 4-177 OCH ₂ CH ₂ SO ₂ Me Me 2 c ₂ f ₅ 4-178 OCH ₂ CH ₂ SO ₂ Me Et 2 c ₂ f ₅ 4-179 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 c ₂ f _s 4-180 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 c ₂ f ₅ 4-181 OMe Me 0 CCij 4-182 OMe Et 0 CCij 4-183 OMe n-Pr 0 CC! ₃ 4-184 OMe i-Pr 0 CCI ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-185 OMe Me 1 CCI ₃ 4-186 OMe Et 1 CCI ₃ 4-187 OMe n-Pr 1 CCI ₃ 4-188 OMe i-Pr 1 CCI ₃ 4-189 OMe Me 2 CCI ₃ 4-190 OMe Et 2 CCIj 4-191 OMe n-Pr 2 CCI ₃ 4-192 OMe i-Pr 2 CCI ₃ 4-193 OEt Me 0 CCIj 4-194 OEt Et 0 CCI, 4-195 OEt n-Pr 0 CCI ₃ 4-196 OEt i-Pr 0 CCIj 4-197 OEt Me 1 CCIj 4-198 OEt Et 1 CCIj 4-199 OEt n-Pr 1 CCI ₃ 4-200 OEt i-Pr 1 CCI ₃ 4-201 OEt Me 2 CCI ₃ 4-202 OEt Et 2 CCI ₃ 4-203 OEt n-Pr 2 CCI ₃ 4-204 OEt i-Pr 2 CCI ₃ 4-205 0CH ₂ -c-Pr Me 0 CCIj 4-206 OCH ₂ -c-Pr Et 0 CCIj 4-207 OCHj-c-Pr n-Pr 0 CCIj 4-208 OCH; -c-Pr i-Pr 0 CCIj 4-209 OCH ₂ -oPr Me 1 CCIj 4-210 OCH ₂ -c-Pr Et 1 CCI ₃ 4-211 OCHj-c-Pr n-Pr 1 CCIj 4-212 OCH ₂ -c-Pr i-Pr 1 CCIj 4-213 OCH ₂ -c-Pr Me 2 CCIj 4-214 OCH ₂ -c-Pr Et 2 CCIj 4-215 OCH ₂ -c-Pr n-Pr 2 CCIj

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Nr. X R ’ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-216 OCHj-c-Pr i-Pr 2 CCI ₃ 4-217 OCH ₂ CH ₂ OMe Me 0 CCI ₃ 4-218 OCH ₂ CH ₂ OMe Et 0 CCIi 4-219 OCH ₂ CH ₂ OMe n-Pr 0 CCIj 4-220 OCH ₂ CH ₂ OMe i-Pr 0 CCI ₃ 4-221 OCHiCHjOMe Me 1 CCI ₃ 4-222 OCHjCHjOMe Et 1 CCI ₃ 4-223 OCH ₂ CH ₂ OMe n-Pr 1 CCI ₃ 4-224 OCH ₂ CH ₂ OMe i-Pr 1 CCI ₃ 4-225 OCH ₂ CH ₂ OMe Me 2 CCI ₃ 4-226 OCH ₂ CH ₂ OMe Et 2 CCÍ ₃ 4-227 OCH ₂ CH ₂ OMe n-Pr 2 CCI ₃ 4-228 OCH ₂ CH ₂ OMe i-Pr 2 CCh 4-229 OCH ₂ CH ₂ SMe Me 0 CCIs 4-230 OCH ₂ CH ₂ SMe Et 0 CCIs 4-231 OCH ₂ CH _z SMe n-Pr 0 CCIj 4-232 OCH ₂ CH ₂ SMe i-Pr 0 CCIj 4-233 OCH ₂ CH ₂ SMe Me 1 CCIs 4-234 OCH ₂ CH ₂ SMe Et 1 CCI-, 4-235 OCH ₂ CH ₂ SMe n-Pr 1 CCIs 4-236 OCH ₂ CH ₂ SMe i-Pr 1 CCIs 4-237 OCH ₂ CH ₂ SMe Me 2 CCIs 4-238 OCH ₂ CH ₂ SMe Et 2 CCIs 4-239 OCH _z CH ₂ SMe n-Pr 2 CCIs 4-240 OCH ₂ CH ₂ SMe i-Pr 2 CCIs 4-241 OCH ₂ CH ₂ SO ₂ Me Me 0 CCI ₃ 4-242 OCH ₂ CH ₂ SO ₂ Me Et 0 CCI ₃ 4-243 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CCI ₃ 4-244 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CCI ₃ 4-245 OCH ₂ CH ₂ SO ₂ Me Me 1 CCI ₃ 4-246 OCH _z CH ₂ SO ₂ Me Et 1 CCIs

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 4-247 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CCI ₃ 4-248 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CCI ₃ 4-249 0CH ₂ CH ₂ SO ₂ Me Me 2 CCI ₃ 4-250 OCH ₂ CH ₂ SO ₂ Me Et 2 CCI ₃ 4-251 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CCI ₃ 4-252 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CCIj 4-253 OMe Me 0 chf ₂ 4-254 OMe Et 0 chf ₂ 4-255 OMe n-Pr 0 chf ₂ 4-256 OMe i-Pr 0 chf ₂ 4-257 OMe Me 1 chf ₂ 4-258 OMe Et 1 chf ₂ 4-259 OMe n-Pr 1 chf ₂ 4-260 OMe i-Pr 1 chf ₂ 4-261 OMe Me 2 chf ₂ 4-262 OMe Et 2 CHFí 4-263 OMe n-Pr 2 chf ₂ 4-264 OMe i-Pr 2 - chf ₂ 4-265 OEt Me 0 chf ₂ 4-266 OEt Et 0 CHFj 4-267 OEt n-Pr 0 chf ₂ 4-268 OEt i-Pr 0 chf ₂ 4-269 OEt Me 1 chf ₂ 4-270 OEt Et 1 chf ₂ 4-271 OEt n-Pr 1 chf ₂ 4-272 OEt i-Pr 1 CHFí 4-273 OEt Me 2 chf ₂ 4-274 OEt Et 2 chf ₂ 4-275 OEt n-Pr 2 chf ₂ 4-276 OEt i-Pr 2 chf ₂ 4-277 O-CH ₂ -c-Pr Me 0 chf ₂ 4-278 O - CH ₂ - c-Pr Et 0 chf ₂ 4-279 O - CH ₂ - c-Pr n-Pr 0 chf ₂

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Nr. X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-280 O - CH ₂ - c-Pr i-Pr 0 chf ₂ 4-281 0 - CH ₂ - c-Pr Me 1 CHFj 4-282 O-CH ₂ -c-Pr Et 1 chf ₂ 4-283 O-CH _z -c-Pr n-Pr 1 chf ₂ 4-284 O-CH ₂ -c-Pr í-Pr 1 CHFj 4-285 O-CH ₂ -c-Pr Me 2 CHFj 4-286 0-CH ₂ -cPr Et 2 CHFj 4-287 O-CH ₂ -c-Pr n-Pr 2 CHFj 4-288 O-CHj-c-Pr Í-Pr 2 chf ₂ 4-289 OCH ₂ CH ₂ OMe Me 0 chf ₂ 4-290 QCHjCHjOMe Et 0 CHFj 4-291 OCH ₂ CH ₂ OMe n-Pr 0 CHFj 4-292 OCHjCHjQMe i-Pr 0 CHFj 4-293 OCH ₂ CH ₂ OMe Me 1 CHFj 4-294 OCHjCHjOMe Et 1 CHFj 4-295 OCHjCHjOMe n-Pr 1 CHFj 4-298 OCHjCHjOMe i-Pr 1 chf ₂ 4-297 OCHjCHjOMe Me 2 chf ₂ 4-298 OCHjCHjOMe Et 2 chf ₂ 4-299 OCH ₂ CH ₂ OMe n-Pr 2 chf ₂ 4-300 OCHjCHjOMe i-Rr 2 chf ₂ 4-301 OCH ₂ CH ₂ 3Me Me 0 CHFj 4-302 OCHjCHjSMe Et 0 CHFj 4-303 OCH ₂ CH ₂ SMe n-Pr 0 chf ₂ 4-304 OCHjCHjSMe i-Pr 0 CHFj 4-305 OCH ₂ CH ₂ SMe Me 1 CHFj 4-306 OCH ₂ CH ₂ SMe Et 1 chf ₂ 4-307 OCH ₂ CH ₂ SMe n-Pr 1 CHFj 4-308 OCHjCHjSMe i-Pr 1 CHFj 4-309 OCH ₂ CH ₂ SMe Me 2 CHFj 4-310 OCH ₂ CH ₂ SMe Et 2 CHFj 4-311 OCHjCHjSMe n-Pr 2 chf ₂ 4-312 OCHjCHjSMe i-Pr 2 CHFj

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-313 OCH ₂ CH ₂ SO ₂ Me Me 0 chf ₂ 4-314 OCH ₂ CH ₂ SO ₂ Me Et 0 chf ₂ 4-315 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 chf ₂ 4-316 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 chf ₂ 4-317 QCH ₂ CH ₂ SO ₂ Me Me 1 chf ₂ 4-318 OCH ₂ CH ₂ SO ₂ Me Et 1 chf ₂ 4-319 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 chf ₂ 4-320 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 chf ₂ 4-321 OCH ₂ CH ₂ SO ₂ Me Me 2 chf ₂ 4-322 OCH ₂ CH ₂ SO ₂ Me Et 2 chf ₂ 4-323 OCH ₂ CH ₂ SO ₂ Me n-Rr 2 chf ₂ 4-324 OCH ₂ CH ₂ SO _z Me i-Pr 2 chf ₂ 4-325 OMe Me 0 CF (CF ₃ ) ₃ 4-326 OMe Et 0 CF (CFs) ₂ 4-327 OMe n-Rr 0 CF (CFs) ₂ 4-328 OMe i Pr 0 CF (CF ₃ ) ₂ 4-329 OMe Me 1 CF (CF ₃ ) ₂ 4-330 OMe Et 1 CF (CF _s ) ₂ 4-331 OMe n-Pr 1 CF (CFs) ₂ 4-332 OMe i-Pr 1 CF (CFj) ₂ 4-333 OMe Me 2 CF (CFs) ₂ 4-334 OMe Et 2 CF (CFj) ₂ 4-335 OMe n-Pr 2 CF (CF ₃ ) ₃ 4-336 OMe í-Pr 2 CF (CF _s ) ₂ 4-337 OEt Me 0 CF (CFs) ₂ 4-338 OEt Et 0 CF (CF ₃ ) ₃ 4-339 OEt n-Pr 0 CF (CFs) ₂ 4-340 OEt i-Pr 0 CF (CF ₃ ) ₃ 4-341 OEt Me 1 CF (CF ₃ ) ₂ 4-342 OEt Et 1 CF (CFs) ₂ 4-343 OEt n-Pr 1 CF (CF ₃ ) ₃ 4-344 OEt i-Pr 1 CF (CFs) ₂ 4-345 OEt Me 2 CF (CF ₃ ) _z

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-346 OEt Et 2 CF (CF _a ) ₂ 4-347 OEt n-Pr 2 CF (CF,) ₂ 4-348 OEt i-Pr 2 cf <cf ₃ > ₂ 4-349 O-CH _z -c-Pr Me 0 CF (CF ₃ } ₂ 4-350 O - CH ₂ - c-Pr Et 0 CF (CF,} ₂ 4-351 0 - CH ₂ - c-Pr n-Pr 0 CF (CF ₃ } ₂ 4-352 O - CH ₂ - c-Pr i-Pr 0 CF (CF ₃ ) ₂ 4-353 O - CHj - c-Pr Me 1 CF (CF ₃ ) j 4-354 O - CH, - c-Pr Et 1 CF (CF ₃ ) ₂ 4-355 O - CH ₂ - c-Pr n-Pr 1 CF (CF ₃ ) ₂ 4-356 O - CH ₂ - c-Pr i-Pr 1 CF (CF ₃ ) ₂ 4-357 O - CH ₂ - c-Pr Me 2 CF (CF ₃ ) ₂ 4-356 O - CH, - c-Pr Et 2 CF (CF,) ₂ 4-359 O - CH ₂ - c-Pr n-Pr 2 CF (CFj) ₂ 4-360 O - CH ₂ - c-Pr i-Pr 2 CF (CF ₃ ) ₂ 4-361 OCH ₂ CH ₂ OMe Me 0 CF (CF,) ₂ 4-362 OCH ₂ CH ₂ OMe Et 0 CF (CF _a ) ₂ 4-363 OCH ₂ CH ₂ QMe n-Pr 0 CF (CF ₃ ) ₂ 4-364 OCH ₂ CH ₂ OMe i-Pr 0 CF (CF ₃ ) ₂ 4-365 OCH ₂ CH ₂ OMe Me 1 CF (CF ₃ ) ₂ 4-366 OCH ₂ CH ₂ OMe Et 1 CF (CF ₃ ) ₂ 4-367 OCH ₂ CH ₂ OMe n-Pr 1 CF (CF ₃ ) ₂ 4-368 OCH ₂ CH ₂ OMe i-Pr 1 CF (CF ₃ ) ₂ 4-369 OCH ₂ CH ₂ OMe Me 2 CF (CF ₃ ) ₂ 4-370 OCH ₂ CH ₂ OMe Et 2 CF (CF ₃ ) ₂ 4-371 OCH ₂ CH ₂ OMe n-Pr 2 CF (CF ₃ ) ₂ 4-372 OCH ₂ CH ₂ OMe i-Pr 2 CF (CF ₃ ) ₂ 4-373 OCH ₂ CH _z SMe Me 0 CF (CF ₃ ) ₂ 4-374 OCH ₂ CH ₂ SMe Et 0 CF (CF ₃ ) ₂ 4-375 OCH _z CH _z SMe n-Pr 0 CF (CF ₃ ) ₂ 4-376 OCH ₂ CH ₂ SMe i-Pr 0 CF (CF ₃ ) ₂ 4-377 OCH ₂ CH ₂ SMe Me 1 CF (CF ₃ ) ₂ 4-378 OCH ₂ CH ₂ SMe Et 1 CF (CF ₃ ) j

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 4-379 OCH ₂ CH ₂ SMe n-Pr 1 CF (CF,) ₂ 4-380 OCH ₂ CH ₂ SMe i-Pr 1 CF (CF,) ₂ 4-381 OCH ₂ CH ₂ SMe Me 2 CF (CFj) ₂ 4-382 OCH ₂ CH ₂ SMe Et 2 CF (CF,) ₂ 4-383 OCH ₂ CH ₂ SMe n-Pr 2 CF (CF,) ₂ 4-384 OCH ₂ CH ₂ SMe i-Pr 2 CF (CFs) ₂ 4-385 OCH ₂ CH ₂ SO ₂ Me Me 0 CF (CF _s ) ₂ 4-386 OCH ₂ CH ₂ SO ₂ Me Et D CF (CF,) ₂ 4-387 0CH ₂ CH ₂ SO ₂ Me n-Pr D CF (CF,) ₂ 4-388 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CF (CF,) ₂ 4-389 OCH ₂ CH ₂ SO ₂ Me Me 1 CF (CF,) ₂ 4-390 OCH ₂ CH ₂ SO ₂ Me Et 1 CF (CFj) ₂ 4-391 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CF (CF ₃ ) ₂ 4-392 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CF (CF ₃ ) ₂ 4-393 OCH ₂ CH ₂ SO ₂ Me Me 2 CF (CF ₃ ) ₂ 4-394 OCH ₂ CH ₂ SO ₂ Me Et 2 CF (CF ₃ ) ₂ 4-395 OCH ₂ CH ₂ S0 ₂ Me n-Pr 2 cf <cf ₃ ) ₂ 4-396 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CF (CF ₃ } ₂

Table 5: compounds according to the invention, of the general formula (I), in which R ² means hydroxy, R ⁴ , R ⁵ , R ⁶ and R ⁷ , respectively, hydrogen, as well as R ³ and R ⁶ mean, together, an ethylene group.

Nr. X R ' π Y Physical data: ¹ H-NMR: δ [CDCIs] 5-1 OH Me 0 CF ₃ 5-2 OH Et 0 CF ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-3 OH n-Pr 0 cf ₃ 5-4 OH i-Pr 0 CFj 5-5 OH Me 1 CFj 5-6 OH Et 1 CFj 5-7 OH n-Pr 1 CFj 5-8 OH i-Pr 1 CFj 5-9 OH Me 2 CFj 5-10 OH Et 2 CFj 5-11 OH n-Pr 2 CFj 5-12 OH i-Pr 2 CFj 5-13 OMe Me 0 CFj 5-14 OMe Et 0 CFj 5-15 OMe n-Pr 0 CFj 5-16 OMe i-Pr 0 CFj 5-17 OMe Me 1 CFj 16.68 (s, 1H), 7.56 (m, 1H), 7.42 <d _f 1H), 3.85 / 3.83 (s, 3H). 3.17 (m, 1H), 3.09 / 3.07 (s, 3H), 2.92 (m, 1H), 2.32— 1.62 (m, 6H) 5-18 OMe Et 1 CFj 5-19 OMe n-Pr 1 CFj 5-20 OMe i-Pr 1 CFj 5-21 OMe Me 2 CFj 16.68 (S, 1H), 7.72 (d, 1H), 7.53 (d, 1H). 3.82 (s, 3H), 3.31 (s, 3H), 3.18 (m, 1H), 2.91 (m, 1H), 2.32-2.12 (m, 3H>, 2.03 (m, 1H). 1.81 - 1.71 ( m _r 2H) 5-22 OMe Et 2 CFj 5-23 OMe n-Pr 2 CFj 5-24 OMe i-Pr 2 CFj 5-25 OEt Me 0 CFj 5-26 OEt Et 0 CFj

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-27 OEt n-Pr 0 cf ₃ 5-28 OEt j-Pr 0 CFj 5-29 OEt Me 1 CFj 5-30 OEt Et 1 CFj 5-31 OEt n-Pr 1 CFj 5-32 OEt i-Pr 1 CF ₃ 5-33 OEt Me 2 CFj 5-34 OEt Et 2 CFj 5-35 OEt n-Pr 2 CFj 5-36 OEt i-Pr 2 CFj 5-37 O-CH ₂ -c-Pr Me 0 CFj 5-38 O-CH ₃ -c-Pr Et 0 CFj 5-39 O-CH ₂ -c-Pr n-Pr 0 CFj 5-40 O-CHj-oPr i-Pr 0 CFj 5-41 O-CI-h-c-Pr Me 1 CFj 5-42 O - CH ₂ - c-Pr Et 1 CFj 5-43 O - CH ₂ - c-Pr n-Pr 1 CFj 5-14 O - CHí - c-Pr i-Pr 1 CFj 5-45 O - CHj - c-Pr Me 2 CFj 5-16 O - CH ₂ - c-Pr Et 2 CFj 5-47 O - CHí - c-Pr n-Pr 2 CFj 5-48 O - CHí - c-Pr i-Rr 2 CFj 5-49 OCH ₂ CH ₂ OMe Me 0 CFj 5-50 OCHiCHiOMe Et 0 CFj 5-51 OCH ₂ CHiOMe n-Pr 0 CFj 5-52 OCHiCHiOMe i-Pr 0 CFj 5-53 OCHiCHiOMe Me 1 CFj 5-54 OCHiCHiOMe Et 1 CFj

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-55 OCH ₂ CH ₂ OMe n-Pr 1 CF _a 5-56 OCH ₂ CH ₂ OMe i-Pr 1 CF _a 5-57 OCHjCHíOMe Me 2 CFj 5-58 OCH ₂ CH ₂ OMe Et 2 cf ₃ 5-59 OCH ₂ CH ₂ OMe n-Pr 2 cf ₃ 5-60 OCH ₂ CH ₂ OMe i-Pr 2 cf ₃ 5-61 OCH ₂ CH ₂ SMe Me 0 cf ₃ 5-62 OCH ₂ CH ₂ SMe Et 0 CFj 5-63 OCH ₂ CH ₂ SMe n-Pr 0 cf ₃ 5-64 OCH ₂ CH ₂ SMe i-Pr 0 cf ₃ 5-65 OCH ₂ CH _z SMe Me 1 CFj 5-66 0CH ₂ CH _z SMe Et 1 CFj 5-67 OCH ₂ CH ₂ SMe n-Pr 1 CFj 5-68 0CH ₂ CH _z SMe i-Pr 1 CFj 5-69 OCH ₂ CH ₂ SMe Me 2 CFj 5-70 OCH ₂ CH ₂ SMe Et 2 LL O 5-71 OCH ₂ CH ₂ SMe n-Pr 2 LL O 5-72 OCH ₂ CH ₂ SMe i-Pr 2 CFj 5-73 OCH ₂ CH ₂ SO ₂ Me Me 0 CFj 5-74 OCH ₂ CH ₂ SO _z Me Et 0 LL O 5-75 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CFj 5-76 OCH ₂ CH ₂ SQ ₂ Me i-Pr 0 CFj 5-77 OCK ₂ CH _z SO ₂ Me Me 1 CFj 5-78 OCH ₂ CH _z SO ₂ Me Et 1 CFj 5-79 OCH _s CH ₂ SO ₂ Me n-Pr 1 cf ₃ 5-80 OCH ₂ CH ₂ SOjMe i-Pr 1 CFj 5-81 OCH _z CH ₂ SO ₂ Me Me 2 CFj 5-82 OCH ₂ CH ₂ SO ₂ Me Et 2 CFj

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-83 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 cf ₃ 5-84 OCH ₂ CH; .SO ₂ Me i-Pr 2 CF ₃ 5-85 OCOMe Me 0 CFj 5-86 OCOMe Et 0 cf ₃ 5-87 OCOMe n-Pr 0 cf ₃ 5-88 OCOMe i-Pr 0 cf ₃ 5-89 OCOMe Me 1 cf ₃ 5-90 OCOMe Et 1 cf ₃ 5-91 OCOMe n-Pr 1 cf ₃ 5-92 OCOMe i-Pr 1 cf ₃ 5-93 OCOMe Me 2 cf ₃ 5-94 OCOMe Et 2 CF ₃ 5-95 OCOMe n-Pr 2 cf ₃ 5-96 OCOMe i-Pr 2 cf ₃ 5-97 OSO ₂ Me Me O cf ₃ 5-98 OSO ₂ Me Et 0 cf ₃ 5-99 OSO ₂ Me n-Pr 0 cf ₃ 5-100 OSO ₂ Me i-Pr 0 cf ₃ 5-101 OSO ₂ Me Me 1 cf ₃ 5-102 OSO ₂ Me Et 1 cf ₃ 5-103 OSOjMe n-Pr 1 cf ₃ 5-104 i-Pr 1 cf ₃ 5-105 OSO ₃ Me Me 2 cf ₃ 5-106 OSO _a Me Et 2 cf ₃ 5-107 OSO ₂ Me n-Pr 2 CFí 5-108 OSO ₂ Me i-Pr 2 cf ₃ 5-109 OMe Me O c ₂ f ₅ 5-110 OMe Et 0 c ₂ f ₅

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-111 OMe n-Pr 0 c ₂ f ₅ 5-112 OMe i-Pr 0 c ₂ f ₅ 5-113 OMe Me 1 c ₂ f _b 5-114 OMe Et 1 CjFs 5-115 OMe n-Pr 1 c ₂ f ₅ 5-116 OMe i-Pr 1 c ₂ f ₅ 5-117 OMe Me 2 c ₂ f ₅ 5-118 OMe Et 2 c ₂ f ₅ 5-119 OMe n-Pr 2 c ₂ f _e 5-120 OMe i-Pr 2 c ₂ f _e 5-121 OEt Me 0 c ₂ f _e 5-122 OEt Et 0 c ₂ f _e 5-123 OEt n-Pr 0 c ₂ f ₅ 5-124 OEt i-Pr 0 c ₂ f _s 5-125 OEt Me 1 c ₂ f _s 5-126 OEt Et 1 c ₂ f ₅ 5-127 OEt n-Pr 1 c ₂ f ₅ 5-128 OEt i-Pr 1 c ₂ f ₅ 5-129 OEt Me 2 C ₂ F 5 5-130 OEt Et 2 c ₂ f _e 5-131 OEt n-Pr 2 c ₂ f ₅ 5-132 OEt i-Pr 2 c ₂ f _e 5-133 OCH ₂ -c-Pr Me 0 c ₂ f ₅ 5-134 OCH ₂ -c-Pr Et 0 c ₂ f ₅ 5-135 OCH ₂ -c-Pr n-Pr 0 c ₂ f ₅ 5-136 OCH _r c-Pr i-Pr 0 c ₂ f ₅ 5-137 OCH _z -c-Pr Me 1 c ₂ f ₅ 5-138 OCH ₂ -c-Pr Et 1 c ₂ f ₅

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-139 OCHj-c-Pr n-Pr 1 c ₂ f ₅ 5-140 OCH ₂ -c-Pr i-Pr 1 c ₂ f ₅ 5-141 OCH ₂ -c-Pr Me 2 c ₂ f ₅ 5-142 OCH ₂ -c-Pr Et 2 c ₂ f ₅ 5-143 OCH ₂ -c-Pr n-Pr 2 c ₂ f _s 5-144 OCH ₂ -c-Pr Í-Pr 2 c ₂ f _s 5-145 OCH ₂ CH ₂ OMe Me 0 c ₂ f ₅ 5-146 OCH ₂ CH ₂ OMe Et 0 C ₂ F _s 5-147 OCH ₂ CH ₂ OMe n-Pr 0 c ₂ f ₅ 5-148 OCH ₂ CH ₂ OMe i-Pr 0 c ₂ f ₅ 5-149 OCH ₂ CH ₂ OMe Me 1 c ₂ f ₅ 5-150 OCH ₂ CH ₂ OMe Et 1 c ₂ f ₅ 5-151 OCH ₂ CH ₂ OMe n-Pr 1 c ₂ f ₅ 5-152 OCH ₂ CH ₂ OMe i-Pr 1 c ₂ f, 5-153 OCH ₂ CH ₂ OMe Me 2 c ₂ f ₅ 5-154 OCH ₂ CH ₂ OMe Et 2 c ₂ f ₅ 5-155 OCH ₂ CH ₂ OMe n-Pr 2 c ₂ f _s 5-156 OCH ₂ CH ₂ OMe i-Pr 2 c ₂ f ₅ 5-157 OCH ₂ CH ₂ SMe Me 0 c ₂ f ₅ 5-158 OCH ₂ CH ₂ SMe Et 0 c ₂ f ₅ 5-159 OCH ₂ CH ₂ SMe n-Pr 0 c ₂ f ₅ 5-160 OCH ₂ CH ₂ SMe i-Pr 0 c ₂ f ₅ 5-161 OCH ₂ CH ₂ SMe Me 1 c ₂ f _s 5-162 OCH ₂ CH ₂ SMe Et 1 c ₂ f ₅ 5-163 OCH ₂ CH ₂ SMe n-Pr 1 c ₂ f _s 5-164 OCH ₂ CH ₂ SMe i-Pr 1 c ₂ f ₅ 5-165 OCH ₂ CH ₂ SMe Me 2 C ₂ F _s 5-166 OCH ₂ CH ₂ SMe Et 2 c ₂ f ₅

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Nr. X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-167 OCH ₂ CH ₂ SMe n-Pr 2 c ₂ f ₅ 5-168 OCH ₂ CH ₂ SMe i-Pr 2 C ₂ F _s 5-169 OCH ₂ CH ₂ SO ₂ Me Me 0 c ₂ f ₅ 5-170 OCH ₂ CH ₂ SO ₂ Me Et 0 c ₂ f ₅ 5-171 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 c ₂ f ₅ 5-172 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 c ₂ f ₅ 5-173 OCH ₂ CH ₂ SO ₂ Me Me 1 c ₂ f ₅ 5-174 OCH ₂ CH ₂ SO ₂ Me Et 1 c ₂ f ₅ 5-175 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 C ₂ Fj 5-176 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 c ₂ f ₃ 5-177 OCH ₂ CH ₂ SO ₂ Me Me 2 c ₂ f ₅ 5-178 OCH ₂ CH ₂ SO ₂ Me Et 2 c ₂ f ₅ 5-179 OGH ₂ CH ₂ SO ₂ Me n-Pr 2 c ₂ f ₅ 5-160 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 c ₂ f ₃ 5-181 OMe Me 0 CCI ₃ 5-182 OMe Et 0 CCI ₃ 5-183 OMe n-Pr 0 CCI ₃ 5-184 OMe i-Pr 0 CCI ₃ 5-185 OMe Me 1 ccj ₃ 5-186 OMe Et 1 CCÍ ₃ 5-187 OMe n-Pr 1 CCI ₃ 5-186 OMe i-Pr 1 CCI ₃ 5-189 OMe Me 2 CCIs 5-190 OMe Et 2 CCI ₃ 5-191 OMe n-Pr 2 CCI ₃ 5-192 OMe i-Pr 2 CCI ₃ 5-193 OEt Me 0 CCI ₃ 5-194 OEt Et 0 CCI ₃

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Nr X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-195 OEt n-Pr 0 CCI ₃ 5-196 OEt i-Pr 0 CCfe 5-197 OEt Me 1 CCI ₃ 5-198 OEt Et 1 CCI ₃ 5-199 OEt n-Pr 1 CCI ₃ 5-200 OEt r-Pr 1 CCI ₃ 5-201 OEt Me 2 CCI ₃ 5-202 OEt Et 2 CCI ₃ 5-203 OEt n-Pr 2 CCI ₃ 5-204 OEt i-Pr 2 CCI ₃ 5-205 OCHs-c-Pr Me 0 CCIj 5-206 OCHi-C-Pr Et 0 CCfj 5-207 OCHj-c-Pr n-Pr 0 CCI ₃ 5-208 OCKj-c-Pr i-Rr 0 CCI ₃ 5-209 OCHí-c-Pr Me 1 CCIj 5-210 OCH ₂ -c-Pr Et 1 CCI _a 5-211 OCHí-c-Pr n-Pr 1 CCI ₃ 5-212 OCH ₂ -c-Pr i-Pr 1 CCI ₃ 5-213 OCHj-c-Pr Me 2 CCIj 5-214 OCH ₂ -c-Pr Et 2 CCIs 5-215 OCH ₂ -c-Pr n-Pr 2 ccij 5-216 OCH ₂ -c-Pr i-Pr 2 CCb 5-217 OCHjCHjOMe Me 0 ccij 5-21B OCH ₂ CH ₂ OMe Et 0 CCI ₃ 5-219 OCH ₂ CH ₂ OMe n-Pr 0 CCI ₃ 5-220 OCH _z CH ₂ OMe i-Pr 0 CCI ₃ 5-221 OCH ₂ CH ₂ OMe Me 1 CCI ₃ 5-222 OCH ₂ CH ₂ OMe Et 1 CCI ₃ 5-223 OCH ₂ CH ₂ OMe n-Pr 1 CCI ₃

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-224 OCH ₂ CH ₂ OMe í-Pr 1 CC! ₃ 5-225 OCHjCHíOMe Me 2 CCf ₃ 5-226 OCHjCHíOMe Et 2 CCI ₃ 5-227 OCH ₂ CH ₂ OMe n-Pr 2 CCIj 5-228 OCH ₂ CH ₂ OMe i-Pr 2 CCIj 5-229 OCH ₂ CH ₂ SMe Me 0 CCIj 5-230 OCH ₂ CH ₂ SMe Et 0 CCI ₃ 5-231 OCH ₂ CH ₂ SMe n-Pr 0 CCIj 5-232 OCH ₂ CH ₂ SMe í-Pr O CCI ₃ 5-233 OCH ₂ CH ₂ SMe Me 1 CCI ₃ 5-234 OCH ₂ CH ₂ SMe Et 1 CCI ₃ 5-235 OCH ₂ CH ₂ SMe n-Pr 1 CCI ₃ 5-236 OCH ₂ CH ₂ SMe i-Pr 1 CCI ₃ 5-237 OCH ₂ Cl-l ₂ âMe Me 2 CCI ₃ 5-238 OCH ₂ CH ₂ SMe Et 2 CCI ₃ 5-239 OCHjCHíSMe n-Pr 2 CCI ₃ 5-240 OCH ₂ CH ₂ SMe i-Pr 2 CCIj 5-241 OCH ₂ CH ₂ SO ₂ Me Me 0 CCI ₃ 5-242 OCH ₂ CH ₂ SO ₂ Me Et 0 CCI ₃ 5-243 OCH2CH ₂ SO ₂ Me n-Pr 0 CCI ₃ 5-244 OCH ₂ CH ₂ SO ₂ Me i-Rr 0 CCb 5-245 OCH ₂ CH ₂ SO ₂ Me Me 1 CCI ₃ 5-246 OCH ₂ CH ₂ SO ₂ Me Et 1 CCI ₃ 5-247 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CCI ₃ 5-248 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CCI ₃ 5-249 OCH ₂ CH ₂ SO ₂ Me Me 2 CCI ₃ 5-250 OCH ₂ CH ₂ SO ₂ Me Et 2 CCIj 5-251 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CCb

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-252 OCHjCHjSOjMe i-Pr 2 CCI ₃ 5-253 OMe Me 0 CHF; 5-254 OMe Et 0 CHFi 5-255 OMe n-Pr 0 chf ₂ 5-256 OMe i-Pr 0 chf ₂ 5-257 OMe Me 1 CHFj 5-25B OMe Et 1 chf ₂ 5-25S OMe n-Pr 1 chf ₂ 5-260 OMe i-Pr 1 CHFj 5-261 OMe Me 2 CHFj 5-262 OMe Et 2 chf ₂ 5-263 OMe n-Pr 2 chf ₂ 5-264 OMe Í-Pr 2 CHFj 5-265 OEt Me 0 chf ₂ 5-266 OEt Et 0 chf ₂ 5-267 OEt n-Pr D CHFj 5-268 OEt i-Pr 0 chf ₂ 5-269 OEt Me 1 chf ₂ 5-270 OEt Et 1 chf ₂ 5-271 OEt n-Pr 1 CHFj 5-272 OEt i-Pr 1 CHFj 5-273 OEt Me 2 CHFj 5-274 OEt Et 2 CHFj 5-275 OEt n-Pr 2 CHFj 5-276 OEt i-Pr 2 CHFj 5-277 O - CH ₂ - c-Pr Me 0 CHFj 5-278 O - CHí - c-Pr Et 0 CHFj 5-279 O - CHj - c-Pr n-Pr 0 CHFj

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-280 O - CH ₂ - c-Pr i-Pr 0 chf ₂ 5-281 O - CH ₂ - c-Pr Me 1 chf ₂ 5-282 O-CH ₂ -c-Pr Et 1 chf ₂ 5-283 O - CH ₂ - c-Pr n-Pr 1 chf ₂ 5-284 O - CH ₂ - c-Pr i-Pr 1 chf ₂ 5-285 0 - CH ₂ - c-Pr Me 2 chf ₂ 5-286 0 - CH ₂ - c-Pr Et 2 chf ₂ 5-287 O-CH ₂ -c-Pr n-Pr 2 chf ₂ 5-288 O-CH ₂ -c-Rr i-Pr 2 chf ₂ 5-289 OCH ₂ CH ₂ OMe Me 0 chf ₂ 5-290 OCH ₂ CH ₂ OMe Et 0 chf ₂ 5-291 OCH ₂ CH ₂ OMe n-Pr 0 chf ₂ 5-292 OCH ₂ CH ₂ OMe i-Pr 0 chf ₂ 5-293 OCH ₂ CH ₂ OMe Me 1 chf ₂ 5-294 OCH ₂ CH ₂ OMe Et 1 chf ₂ 5-295 OCH ₂ CH ₂ OMe n-Pr 1 chf ₂ 5-296 OCH ₂ CH ₂ OMe i-Pr 1 chf ₂ 5-297 OCH ₂ CH ₂ OMe Me 2 chf ₂ 5-298 OCH ₂ CH ₂ OMe Et 2 chf ₂ 5-299 OCH ₂ CH ₂ OMe n-Pr 2 chf ₂ 5-300 OCH ₂ CH ₂ OMe i-Pr 2 chf ₂ 5-301 OCH ₂ CH ₂ SMe Me 0 CHFí 5-302 OCH ₂ CH ₂ SMe Et 0 chf ₂ 5-303 OCH ₂ CH ₂ SMe n-Pr 0 chf ₂ 5-304 OCH ₂ CH ₂ SMe i-Pr 0 chf ₂ 5-305 OCH ₂ CH ₂ SMe Me 1 chf ₂ 5-306 OCH ₃ CH ₂ 5Me Et 1 chf ₂ 5-307 OCH ₂ CH ₂ SMe n-Pr 1 chf ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs]. . ------ r 5-308 OCH ₂ CH ₂ SMe Ϊ-Pr 1 chf ₂ 5-309 OCH ₂ CH ₂ SMe Me 2 chf ₂ 5-310 OCH ₂ CH ₂ SMe Et 2 chf ₂ 5-311 OCH ₂ CH ₂ SMe n-Pr 2 chf ₂ 5-312 OCH ₂ CH ₂ SMe i-Pr 2 chf ₂ 5-313 OCH ₂ CH ₂ SO _z Me Me 0 chf ₂ 5-314 OCH ₂ CH ₂ SO ₂ Me Et 0 chf ₂ 5-315 OCH ₂ CH ₂ SO _? Me n-Pr 0 chf ₂ 5-316 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 chf ₂ 5-317 OCH ₂ CH _z SO ₂ Me Me 1 chf ₂ 5-318 OCH ₂ CH ₂ SO ₂ Me Et 1 chf ₂ 5-319 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 chf ₂ 5-320 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 chf ₂ 5-321 OCH ₂ CH ₂ SO ₂ Me Me 2 chf ₂ 5-322 OCH ₂ CH ₂ SO ₂ Me Et 2 CHFj 5-323 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 chf ₂ 5-324 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 chf ₂ 5-325 OMe Me 0 CF (CF ₃ ) ₂ 5-326 OMe Et 0 CF (CFj) ₂ 5-327 OMe n-Pr 0 CF (CF ₃ ) ₂ 5-328 OMe i-Pr 0 CF (CFj) ₂ 5-329 OMe Me 1 CF (CF ₃ ) ₂ 5-330 OMe Et 1 CF (CF ₃ ) ₂ 5-331 OMe n-Pr 1 CF (CF ₃ ) ₂ 5-332 OMe i-Pr 1 CF (CF ₃ ) _z 5-333 OMe Me 2 CF (CF ₃ ) ₂ 5-334 OMe Et 2 CF (CF ₃ ) _z 5-335 OMe n-Pr 2 CF (CF ₃ ) ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-336 OMe i-Pr 2 CF (CF ₃ ) ₂ 5-337 OEt Me 0 CF (CF ₃ ) ₂ 5-338 OEt Et 0 CF (CF ₃ ) ₂ 5-339 OEt n-Pr 0 CF (CF ₃ > ₂ 5-340 OEt i-Pr 0 CF (CF ₃ > ₂ 5-341 OEt Me 1 CF (CF ₃ > ₂ 5-342 OEt Et 1 CF (CF ₃ ) ₂ 5-343 OEt n-Pr 1 CF (CF ₃ ) ₂ 5-344 OEt i-Pr 1 CF (CF ₃ ) ₂ 5-345 OEt Me 2 CF (CF ₃ ) ₂ 5-346 OEt Et 2 CF (CF ₃ ) ₂ 5-347 OEt n-Pr 2 CF (CF ₃ ) í 5-348 OEt i-Pr 2 CF (CF ₃ ) ₂ 5-349 O -CH ₂ -i> Pr Me 0 CF (CF ₃ } ₂ 5-350 O_ÇH ₂ -c-Pr Et 0 CF (CF ₃ } ₂ 5-351 O - CH ₂ - c-Pr n-Pr 0 CF (CF ₃ ) ₂ 5-352 O - CH ₂ - c-Pr í-Pr 0 CF (CF ₃ ) ₂ 5-353 O - CH ₂ - c-Pr Me 1 CF (CF ₃ ) ₂ 5-354 O - CHj - c-Pr Et 1 CF (CF ₃ ) ₂ 5-355 O - CH, - c-Pr n-Pr 1 CF (CF ₃ ) ₂ 5-356 O - CH ₂ - c-Pr i-Pr 1 CF (CFí) ₂ 5-357 O-CHj-c-Pr Me 2 CF (CF ₃ ) ₂ 5-358 O - CHj - c-Pr Et 2 CF (CFs) ₂ 5-359 O-CHj-c-Pr n-Pr 2 CF (CF ₃ ) ₂ 5-360 O-CH ₂ -c-Pr i-Pr 2 CF <CF ₃ ) ₂ 5-361 OCH ₂ CH ₂ OMe Me 0 CF (CF ₃ ) ₂ 5-362 OCH ₂ CH ₂ OMe Et 0 CF (CFa) ₂ 5-363 OCH ₂ CH ₂ OMe n-Pr 0 CF (CF ₃ > ₂

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Nr. X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-364 OCHjCHjOMe i-Pr 0 CF (CF ₃ ) ₂ 5-365 OCH ₂ CH ₂ OMe Me 1 CF (CF ₃ ) ₂ 5-366 OCH ₂ CH ₂ OMe Et 1 CF (CF ₃ ) ₂ 5-367 OCH ₂ CH ₂ OMe n-Pr 1 CF (CF ₃ ) ₂ 5-368 OCH ₂ CH ₂ OMe i-Pr 1 CF (CF ₃ ) ₂ 5-369 OCHjCHíOMe Me 2 CF (CF ₃ ) ₂ 5-370 OCH ₂ CH ₂ OMe Et 2 CF (CF ₃ ) ₂ 5-371 OCHjCHjOMe n-Pr 2 CF (CF ₃ ) ₂ 5-372 OCH ₂ CH ₂ OMe i-Pr 2 CF (CF ₃ ) ₂ 5-373 OCHjCHjSMe Me 0 CF (CF ₃ ) ₂ 5-374 OCH ₂ CH ₂ SMe Et 0 CF (CF ₃ ) ₂ 5-375 OCH ₂ CH ₂ SMe n-Pr 0 CF (CF ₃ ) ₂ 5-376 OCHiCHjSMe i-Pr 0 CF (CF ₃ ) ₂ 5-377 OCH ₂ CH ₂ SMe Me 1 CF (CF ₃ ) ₂ 5-378 OCH ₂ CH ₂ SMe Et 1 CF (CF ₃ ) ₂ 5-379 OCH ₂ CH ₂ SMe n-Pr 1 CF (CF ₃ ) ₂ 5-380 OCH ₂ CH ₂ SMe r-Pr 1 CF (CF ₃ ) ₂ 5-381 OCH ₂ CH ₂ SMe Me 2 CF (CF ₃ ) ₂ 5-382 OCH ₂ CH ₂ SMe Et 2 CF (CF ₃ ) ₂ 5-383 OCH ₂ CH ₂ SMe n-Pr 2 CF (CF ₃ ) ₂ 5-384 OCH ₂ CH ₂ SMe i-Pr 2 CF (CF ₃ ) ₂ 5-385 OCH ₂ CH ₂ SO ₂ Me Me 0 CF (CF ₃ ) ₂ 5-386 OCH ₂ CH ₂ SO ₂ Me Et 0 CF (CF ₃ ) ₂ 5-387 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CF (CF ₃ ) ₂ 5-388 OCH ₂ CH ₂ SO ₂ Me í-Pr 0 CF (CF ₃ ) ₂ 5-389 OCH ₂ CH ₂ SO ₂ Me Me 1 CF (CF ₃ } ₂ 5-390 OCH ₂ CH ₂ SO ₂ Me Et 1 CF (CF ₃ ) ₂ 5-391 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CF (CF ₃ ) ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 5-392 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CF (CFj) ₂ 5-393 OCHjCHiSCbMe Me 2 CF (CF ₃ ) ₂ 5-394 OCHjCHjSO ^ Me Et 2 CF (CF ₃ ) ₂ 5-395 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CF (CF ₃ ) ₂ 5-396 OCH ₂ CHÍSO ₂ Me i-Pr 2 CF (CF ₃ ) ₂

Table 6: compounds according to the invention, of the general formula (I), in which R ² means phenylthio and R ³ to R ⁸ , respectively, hydrogen.

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 6-1 OMe Me 0 cf ₃ 6-2 OMe Et 0 cf ₃ 6-3 OMe n-Pr 0 cf ₃ 6-4 OMe i-Pr 0 cf ₃ 6-5 OMe Me 1 cf ₃ 6-6 OMe Et 1 cf ₃ 6-7 OMe n-Pr 1 cf ₃ 6-8 OMe i-Pr 1 CFj 6-9 OMe Me 2 cf ₃ 6-10 OMe Et 2 CFj 6-11 OMe n-Pr 2 CFj 6-12 OMe i-Pr 2 cf ₃ 6-13 OEt Me 0 CFj 6-14 OEt Et 0 CFj 6-15 OEt n-Pr 0 CFj 6-16 OEt i-Pr 0 CFj 6-17 OEt Me 1 CFj 6-18 OEt Et 1 CFj

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6-19 OEt n-Pr 1 CFj 6-20 OEt i-Pr 1 CFs 6-21 OEt Me 2 CFs 6-22 OEt Et 2 CFj 6-23 OEt n-Pr 2 CF _a 6-24 OEt t-Pr 2 CF ₃ 6-25 OCH ₂ CH ₂ OMe Me 0 CFs 6-26 OCH ₂ CH ₂ OMe Et 0 CF _a 6-27 OCH ₂ CH ₂ OMe n-Pr O CF ₃ 6-2B QCH ₂ CH ₂ OMe i-Pr 0 CF ₃ 6-20 OCH ₂ CH ₂ OMe Me 1 CFs 6-30 OCH ₂ CH ₂ OMe Et 1 CF ₃ 6-31 OCH _z CH ₂ OMe n-Pr 1 CFj 6-32 OCH ₂ CH ₂ OMe i-Pr 1 CFj 6-33 OCH ₂ CH ₂ OMe Me 2 CFj 6-34 OCH ₂ CH ₂ QMe Et 2 CFs 6-35 OCH ₂ CH ₂ OMe n-Pr 2 CFs 6-36 OCH ₂ CH ₂ OMe i-Pr 2 CFj

Table 7: compounds according to the invention, of the general formula (I), where R ² means phenylthio, R ³ and R ⁴ mean, respectively, methyl, as well as R ⁵ to R ⁸ mean,

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 7-1 OMe Me 0 CFj 7-2 OMe Et D CFj 7-3 OMe n-Pr 0 CFs 7-4 OMe i-Pr 0 CFs 7-5 OMe Me 1 CFj 7-6 OMe Et 1 CFs

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7-7 OMe n-Pr 1 CFj 7-8 OMe i-Pr 1 CFj 7-9 OMe Me 2 CF _a 7-10 OMe Et 2 cf ₃ 7-11 OMe n-Pr 2 CF ₃ 7-12 OMe i-Pr 2 cf ₃ 7-13 OEt Me 0 cf ₃ 7-14 OEt Et 0 cf ₃ 7-15 OEt n-Pr 0 cf ₃ 7-1S OEt i-Pr 0 CFj 7-17 OEt Me 1 CFj 7-18 OEt Et 1 CFj 7-19 OEt n-Pr 1 CFj 7-20 OEt i-Pr 1 CFj 7-21 OEt Me 2 CFj 7-22 OEt Et 2 CFj 7-23 OEt n-Pr 2 CFj 7-24 OEt i-Pr 2 CFj 7-25 OCH ₂ CH ₂ OMe Me 0 CFj 7-26 OCH ₂ CH ₂ OMe Et 0 CFj 7-27 OCH ₂ CH ₂ OMe n-Pr 0 CFj 7-28 OCH ₂ CH ₂ OMe i-Pr 0 CFj 7-29 OCHjCHíOMe Me 1 LL O i 7-30 OCHiCHzOMe Et 1 CF ₃ 7-31 OCH ₂ CH ₂ OMe n-Pr 1 cf ₃ 7-32 OCH ₂ CH ₂ OMe i-Pr 1 CFj 7-33 OCH ₂ CH ₂ OMe Me 2 CFj 7-34 OCH ₂ CH ₂ OMe Et 2 cf ₃ 7-35 OCH ₂ CH ₂ OMe n-Pr 2 CFj 7-36 OCH ₂ CH ₂ OMe i-Pr 2 CFj

Table 8: compounds according to the invention, of the general formula (I), in which R ² means phenylthio, R ³ , R ⁴ , R ⁷ and R ⁸ mean, respectively, hydrogen, as well as R ⁵ and R ⁶ mean, methyl.

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 8-1 OMe Me 0 cf ₃ 8-2 OMe Et 0 CF-, 8-3 OMe n-Pr 0 cf ₃ 8-4 OMe i-Pr 0 cf ₃ 8-5 OMe Me 1 cf ₃ 8-6 OMe Et 1 cf ₃ 8-7 OMe n-Pr 1 cf ₃ 8-8 OMe i-Pr 1 cf ₃ 8-9 OMe Me 2 cf ₃ 8-10 OMe Et 2 CFj 8-11 OMe n-Pr 2 CFj 8-12 OMe i-Pr 2 CFj 8-13 OEt Me 0 CFj 8-14 OEt Et 0 cf ₃ 8-15 OEt n-Pr 0 CFj 8-16 OEt i-Pr 0 CFj 8-17 OEt Me 1 CFj 8-18 OEt Et 1 CFj 8-1S OEt n-Pr 1 CFj 8-20 OEt i-Pr 1 CFj 8-21 OEt Me 2 CFj 8-22 OEt Et 2 CFj 8-23 OEt n-Pr 2 CFj 8-24 OEt i-Pr 2 CFj 8-25 OCH ₂ CH ₂ OMe Me 0 CFj 8-26 OCH ₂ CHjOMe Et 0 CFj 8-27 OCHjCHjOMe n-Pr 0 cf ₃ 8-28 OCHjCHjOMe i-Pr 0 CFj 8-29 OCHjCHjOMe Me 1 cf ₃ 8-30 OCHjCHjOMe Et 1 CFj 8-31 OCH ₂ CH ₂ OMe n-Pr 1 cf ₃ 8-32 OCH ₂ CH ₂ OMe i-Pr 1 cf ₃ 8-33 OCHjCHjOMe Me 2 cf ₃ 8-34 OCHjCHjOMe Et 2 cf ₃ 8-35 OCH ₂ CH ₂ OMe n-Pr 2 cf ₃ 8-36 OCH ₂ CH ₂ QMe i-Pr 2 cf ₃

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Table 9: compounds according to the invention, of the general formula (I), where R ²

means phenylthio, R ³ to R ⁶ , respectively, hydrogen, as well as R ⁷ and R ⁸ mean, respectively, methyl. OCX , SCLR ¹ 1Ί Líτ li í (I) ^s Y ^H to ^C CH, Ph

Nr. X R ’ n Y Physical data: ¹ H-NMR: δ [CDCIs] 9-1 OMe Me 0 CFj 9-2 OMe Et 0 CFj 9-3 OMe n-Pr 0 CFj 9-4 OMe i-Pr 0 CFj 9-5 OMe Me 1 CFj 9-6 OMe Et 1 CFj 9-7 OMe n-Pr 1 CFj 9-8 OMe i-Pr 1 CFj 9-9 OMe Me 2 CFj 9-10 OMe Et 2 CFj 9-11 OMe n-Pr 2 CFj 9-12 OMe í-Pr 2 CFj 9-13 OEt Me 0 CFs 9-14 OEt Et 0 CFj 9-15 OEt n-Pr 0 CFj 9-16 OEt i-Pr 0 CFj 9-17 OEt Me 1 CFj 9-18 OEt Et 1 CFj 9-19 OEt n-Pr 1 CFj 9-20 OEt i-Pr 1 CFj 9-21 OEt Me 2 CFj 9-22 OEt Et 2 CFj 9-23 OEt n-Pr 2 CFj 9-24 OEt i-Pr 2 CFj 9-25 OCH ₂ OH ₂ OMe Me 0 CFj

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9-26 OCH ₂ CH ₂ OMe Et 0 CF ₃ 9-27 OCH ₂ CH ₂ OMe n-Pr 0 cf ₃ 9-28 OCH ₂ CH ₂ OMe i-Pr 0 cf ₃ 9-29 OCHiCH _z OMe Me 1 cf ₃ 9-30 OCH ₂ CH ₂ OMe Et 1 cf ₃ 9-31 OCH ₂ CH ₂ OMe n-Pr 1 cf ₃ 9-32 OCH ₂ CH ₂ OMe i-Pr 1 cf ₃ 9-33 OCH ₂ CH ₂ OMe Me 2 CFs 9-34 OCH ₂ CH ₂ OMe Et 2 CF ₃ 9-35 OCH ₂ CH ₂ OMe n-Pr 2 cf ₃ 9-36 OCH ₂ CH ₂ OMe i-Pr 2 cf ₃

Table 10: compounds according to the invention, of the general formula (I), where R ² means phenylthio, R ³ , R ⁴ , R ⁵ , R ⁷ and R ⁸ respectively, hydrogen, as R ⁶ means, respectively, methyl O

SO R

d)

Nr, X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 10-1 OMe Me 0 CF ₃ 10-2 OMe Et 0 cf ₃ 10-3 OMe n-Pr 0 cf ₃ 10-4 OMe i-Pr 0 CF ₃ 10-5 OMe Me 1 CFj 10-6 OMe Et 1 CFj 10-7 OMe n-Pr 1 CFj 10-8 OMe i-Pr 1 CFj 10-9 OMe Me 2 CFj yo-yo OMe Et 2 CFj 10-11 OMe n-Pr 2 cf ₃ 10-12 OMe i-Pr 2 CF _a 10-13 OEt Me 0 CF _a 10-14 OEt Et 0 CF ₃ 10-15 OEt n-Pr 0 CFa

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10-16 OEt i-Pr 0 CF, 10-17 OEt Me 1 CF ₃ 10-18 OEt Et 1 cf ₃ 10-19 OEt n-Pr 1 cf ₃ 10-20 OEt i-Pr 1 CF _a 10-21 OEt Me 2 cf ₃ 10-22 OEt Et 2 CF, 10-23 OEt n-Pr 2 CF, 10-24 OEt i-Pr 2 CF, 10-25 OCH ₂ CH ₂ OMe Me 0 CF, 10-26 OCHjCH? OMe Et 0 CF, 10-27 OCH ₂ CH ₂ OMe n-Pr 0 CF, 10-28 OCH ₂ CH ₂ OMe i-Pr 0 CF, 10-29 OCH ₂ CH ₂ OMe Me 1 CF, 10-30 OCH ₂ CH ₂ OMe Et 1 CF, 10-31 OCH ₂ CH ₂ OMe n-Pr 1 CF, 10-32 OCH ₂ CH ₂ OMe i-Pr 1 CF, 10-33 OCHjCHj-OMe Me 2 CF, 10-34 OCH ₂ CH ₂ OMe Et 2 CF, 10-35 OCH ₂ CH ₂ OMe n-Pr 2 CF, 10-36 OCHjCHíOMe i-Pr 2 CF,

Table 11: compounds according to the invention, of the general formula (I), in which R ² means phenylthio, R ⁴ , R ⁵ , R ⁶ and R ⁷ , respectively, hydrogen, just as R ³ and R ⁸ mean, together, an ethylene group.

(D

Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 11-1 OMe Me 0 CF, 11-2 OMe Et 0 CF, 11-3 OMe n-Pr 0 CF, 11-4 OMe i-Pr 0 CF, 11-5 OMe Me 1 CF, 11-6 OMe Et 1 CF, 11-7 OMe n-Pr 1 CF,

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11-8 OMe i-Pr 1 CFj 11-9 OMe Me 2 cf ₃ 11-10 OMe Et 2 CFj 11-11 OMe n-Pr 2 cf ₃ 11-12 OMe i-Pr 2 cf ₃ 11-13 OEt Me 0 CFj 11-14 OEt Et 0 CR 11-15 OEt n-Pr 0 CFj 11-16 OEt i-Pr 0 CR 11-17 OEt Me 1 CR 11-18 OEt Et 1 CF ₃ 11-19 OEt n-Pr 1 cf ₃ 11-20 OEt i-Pr 1 cr 11-21 OEt Me 2 cf ₃ 11-22 OEt Et 2 cf ₃ 11-23 OEt n-Pr 2 cf ₃ 11-24 OEt i-Pr 2 cf ₃ 11-25 OCHjChbOMe Me 0 CR 11-26 OCH ₂ CH ₂ OMe Et 0 cf ₃ 11-27 OCH ₂ CH? OMe n-Pr 0 cf ₃ 11-28 OCHjCHjOMe i-Pr 0 cf ₃ 11-29 OCH ₂ CH ₂ OMe Me 1 cf ₃ 11-30 OCH ₂ CH ₂ OMe Et 1 cf ₃ 11-31 OCH ₂ CH ₂ OMe n-Pr 1 CF _a 11-32 OCH ₂ CH ₂ OMe i-Pr 1 CR 11-33 OCH ₂ CH ₂ OMe Me 2 CF ₃ 11-34 OCH ₂ CH ₂ OMe Et 2 CR 11-35 OCH ₂ CH ₂ OMe n-Pr 2 CR 11-36 OCH ₂ CH ₂ OMe i-Pr 2 cf ₃

Table 12: compounds according to the invention, of the general formula (II)

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-1 OH Me 0 CFj 12-2 OH Et 0 cf ₃ 12-3 OH n-Pr 0 cf ₃ 12-4 OH i-Pr 0 cf ₃ Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 12-5 OH Me 1 cf ₃ 12-6 OH Et 1 CF ₃ 12-7 OH n-Pr 1 CF _â 12-8 OH i-Pr 1 cf ₃ 12-9 OH Me 2 cf ₃ 12-10 OH Et 2 cf ₃ 12-11 OH n-Pr 2 cf ₃ 12-12 OH i-Pr 2 cf ₃ 12-13 OMe Me 0 LL O 7.76 (d, 1H), 7.58 (d, 1H). 3.91 ($, 3H), 2.40 (s. 3H) 12-14 OMe Et 0 cf ₃ 7.78 (d, 1H), 7.61 (d, 1H), 3.90 (s, 3H), 2 95 (q, 2H), 1.07 (t, 3H) 12-15 OMe n-Pr 0 cf ₃ 12-16 OMe i-Pr 0 cf ₃ 12-17 OMe Me 1 cf ₃ 12-10 OMe Et 1 cf ₃ 12-19 OMe n-Pr 1 cf ₃ 12-20 OMe i-Pr 1 cf ₃ 12-21 OMe Me 2 cf ₃ 12-22 OMe Et 2 cf ₃ 12-23 OMe n-Pr 2 cf ₃ 12-24 OMe i-Pr 2 CFj 12-25 OEt Me 0 cf ₃ 7.78 (d, 1H), 7.60 (d, 1H), 4.12 (q, 2H), 2.43 (s, 3H), 1.37 (t, 3H) 12-26 OEt Et 0 I LL O 7.78 (d. 1H), 7.61 (d, 1H>, 4.12 (q, 2H). 2.98 (q. 2H} _t 1.36 (t, 3H), 1.08 (t, 3H) 12-27 OEt n-Pr 0 cf ₃ 12-28 OEt i-Pr 0 cf ₃

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12-29 OEt Me 1 cf ₃ 12-30 OEt Et 1 cf ₃ 12-31 OEt n-Pr 1 CFj 12-32 OEt i-Pr 1 CFj 12-33 OEt Me 2 CFj Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-34 OEt Et 2 CFj 12-35 OEt n-Pr 2 CFj 12-36 OEt i-Pr 2 CFj 12-37 O - CH ₂ - c-Pr Me 0 CFj 7.77 (d, 1H) _f 7.60 (d, 1H), 3.92 {d, 2H), 2:46 (s, 3H), 1.27 (m, 1H). 0.57 (m, 2H), 0.33 (m, 2H) 12-38 O — CHj —c-Pr Et 0 CFj 12-39 O-CH ₂ -c-Pr n-Pr 0 CFj 12-40 O - CH ₂ - c-Pr i-Pr 0 CFj 12-41 O - CHí - c-Pr Me 1 CFj 12-42 O - CH ₃ - c-Pr Et 1 CFj 12-43 O - CH ₂ - c-Pr n-Pr 1 CFj 12-44 O - CH ₂ - c-Pr i-Pr 1 CFj 12-45 O - CH ₂ - c-Pr Me 2 CFj 12 46 O-CH ₂ -c-Pr Et 2 CFj 12-47 O-CH ₂ -c-Pr n-Pr 2 CFj 12-48 O - CH ₂ - c-Pr i-Pr 2 CFj 12-4S OCH ₂ CH ₂ OMe Me 0 CFj 7.77 (d, 1H), 760 (d, 1H), 4.22 {t. 2H>, 3.71 <t, 2H), 2.44 (s, 3H) 12-50 OCHiCHjOMe Et 0 CFj 12-51 OCH ₂ CH ₂ OMe n-Pr 0 CFj 12-52 OCHjCHjOMe i-Pr 0 CFj 12-53 OCH ₂ CH ₂ OMe Me 1 CFj 12-54 OCHjCHjOMe Et 1 CFj 12-55 OCK ₂ CH ₂ OMe n-Pr 1 CF, 12-56 OCH ₂ CH ₂ OMe i-Pr 1 CFj 12-57 OCH ₂ CH ₂ OMe Me 2 CF,

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12-58 OCH ₂ CH ₂ OMe Et 2 CF, 12-59 OCH ₂ CH ₂ OMe n-Pr 2 CF, 12-60 OCHjCHjOMe i-Pr 2 CF, 12-61 OCH ₂ CH ₂ SMe Me 0 CF, 12-62 OCH ₂ CH ₂ SMe Et 0 CF, 12-63 OCHjCHjSMe n-Pr 0 CF, Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-64 OCH ₂ CH ₂ SMe í-Pr 0 CF, 12-65 OCHjCHjSMe Me 1 CF, 12-66 OCH ₂ CH ₂ SMe Et 1 CF, 12-67 OCH ₂ CH ₂ SMe n-Pr 1 CF, 12-68 OCHjCHjSMe i-Pr 1 CF, 12-69 OCH ₂ CH ₂ SMe Me 2 CF, 12-70 OCHjCH ₂ SMe Et 2 CF, 12-71 OCHjCHjSMe n-Pr 2 CF, 12-72 OCHjCHjSMe i-Pr 2 CF, 12-73 OCH ₂ CHjSO ₂ Me Me 0 CF, 12-74 OCH ₂ CH ₂ SO ₂ Me Et 0 CF, 12-75 OCHjCHjSOjMe n-Pr 0 CF, 12-76 QCHjCHjSQjMe i-Pr 0 CF, 12-77 OCH ₂ CH ₂ SO ₂ Me Me 1 CF, 12-78 OCHjCHjSOjMe Et 1 CF, 12-79 OCH ₂ CHjSO ₂ Me n-Pr 1 CF, 12-80 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 CF, 12-81 OCHjCHjSOjMe Me 2 CF, 12-82 OCHjCHjSOjMe Et 2 CF, 12-83 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CF, 12-84 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CF, 12-85 OCOMe Me 0 CF, 12-86 OCOMe Et 0 CF, 12-87 OCOMe n-Pr 0 CF, 12-88 OCOMe í-Pr 0 CF, 12-89 OCOMe Me 1 CF, 12-90 OCOMe Et 1 CF,

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12-91 OCOMe n-Pr 1 CFj 12-92 OCOMe i-Pr 1 CFj 12-93 OCOMe Me 2 CFj 12-94 OCOMe Et 2 CFj 12-95 OCOMe n-Pr 2 CFj 12-96 OCOMe i-Pr 2 CFj Nr, X R ¹ n Y Physikalische Daten; ¹ H-NMR; õ [DMSO-de] 12-97 OSOjMe Me 0 CFj 12-98 OSOjMe Et 0 CFj 12-99 OSO _z Me n-Pr 0 CFj 12-100 OSOíMe i-Pr 0 CFj 12-101 OSO ₂ Me Me 1 CFj 12-102 OS0 ₂ Me Et 1 CFj 12-103 OSO ₂ Me n-Pr 1 CFj 12-104 OSO ₂ Me i-Pr 1 CFj 12-105 OSO ₃ Me Me 2 CFj 12-106 OSO ₃ IWe Et 2 CFj 12-107 OSO ₂ Me n-Pr 2 CFj 12-108 OSO ₂ Me i-Pr 2 CFj 12-109 OMe Me 0 c ₂ f ₅ 12-110 OMe Et 0 c ₂ f ₅ 12-111 OMe n-Pr 0 c ₂ f ₅ 12-112 OMe i-Pr 0 c ₂ f _s 12-113 OMe Me 1 c ₂ f _s 12-114 OMe Et 1 c ₂ f ₅ 12-115 OMe n-Pr 1 c ₂ f ₅ 12-116 OMe i-Pr 1 c ₂ f ₅ 12-117 OMe Me 2 c ₂ f ₅ 12-118 OMe Et 2 C; Fs 12-119 OMe n-Pr 2 c ₂ f ₅ 12-12D OMe i-Pr 2 c ₂ f ₅ 12-121 OE1 Me 0 c ₂ f ₅ 12-122 OEt Et 0 c ₂ f _s 12-123 OEt n-Rr 0 c ₂ f ₅ 12-124 OEt i-Pr 0 c ₂ f ₅ 12-125 OEt Me 1 c ₂ f ₅

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12-126 OEt Et 1 c ₂ f ₅ 12-127 OEt n-Pr 1 c ₂ f ₅ 12-128 OEt i-Pr 1 c ₂ f ₅ 12-129 OEt Me 2 c _£ f ₅ Nr. X R ¹ n Y Physikalische Daten: ’H-NMR: õ [DMSO-dd 12-130 OEt Et 2 c ₂ f ₅ 12-131 OEt n-Pr 2 C ₂ F _s 12-132 OEt i-Pr 2 C ₂ F _s 12-133 O - CH ₂ - c-Pr Me 0 c ₂ f ₅ 12-134 O - CH _z - c-Pr Et 0 C ₂ F _s 12-135 O - CH ₂ - c-Pr n-Pr 0 c ₂ f _s 12-136 O - CH ₂ - c-Pr i-Pr 0 C ₂ Fs 12-137 O - CH ₂ - c-Pr Me 1 c ₂ f ₅ 12-138 O - CH _Z - c-Pr Et 1 c ₂ f ₅ 12-139 O - CH _Z - c-Pr n-Pr 1 c ₂ f ₅ 12-140 O - CH ₂ - c-Pr i-Pr 1 c ₂ f ₅ 12-141 O - CH ₂ - c-Pr Me 2 c ₂ f ₅ 12-142 O - CH ₂ - c-Pr Et 2 c ₃ f _& 12-143 O - CH ₂ - c-Pr n-Pr 2 c ₂ f ₅ 12-144 O - CH _Z - c-Pr i-Pr 2 c ₂ f ₅ 12-145 OCH ₂ CH ₂ OMe Me 0 C ₂ Fí 12-146 OCH ₂ CH ₂ OMe Et 0 C _z F _; 12-147 OCH ₂ CH ₂ OMe n-Pr 0 c ₂ f ₅ 12-148 OCH ₂ CH ₂ OMe i-Pr 0 c ₂ f _s 12-149 OCH ₂ CH ₂ OMe Me 1 c ₂ f _s 12-150 OCH ₂ CH ₂ OMe Et 1 c ₂ f _e 12-151 OCH ₂ CH ₂ OMe n-Pr 1 C ₂ F _s 12-152 OCH ₂ CH ₂ OMe i-Pr 1 c ₂ f ₅ 12-153 OCH ₂ CH ₂ OMe Me 2 c ₂ f ₅ 12-154 OCH ₂ CH ₂ OMe Et 2 c ₂ f _s 12-155 OCH ₂ CH ₂ OMe n-Pr 2 c ₂ f ₅ 12-156 OCH ₂ CH ₂ OMe i-Pr 2 c ₂ f ₅ 12-157 OCH ₂ CH ₂ SMe Me 0 c ₂ f _s 12-158 OCH _z CH ₂ SMe Et 0 C ₂ F 5 12-159 OCHjCHíSMe n-Pr 0 c ₂ f ₅ 12-160 OCH ₂ CH ₂ SMe i-Pr 0 c ₂ f ₅ 12-161 OCH ₂ CH ₂ SMe Me 1 c ₂ f ₅ 12-162 OCH _z CHíSMe Et 1 c ₂ f ₅

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Nr. X R ' n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-163 OCH ₂ CH ₂ SMe n-Pr 1 C ₂ F ₅ 12-164 OCH ₂ CH ₂ SMe i-Pr 1 HERE 12-165 OCH ₂ CH ₂ SMe Me 2 c ₂ f ₅ 12-166 OCH ₂ CH ₂ SMe Et 2 HERE 12-167 OCH ₂ CH ₂ SMe n-Pr 2 HERE 12-168 OCH ₂ CH ₂ SMe i-Pr 2 HERE 12-169 OCH ₂ CH ₂ SO ₂ Me Me 0 HERE 12-170 OCH ₂ CH ₂ SO ₂ Me Et 0 HERE 12-171 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 HERE 12-172 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 HERE 12-173 OCH ₂ CH ₂ SO ₂ Me Me 1 HERE 12-174 OCH ₂ CH ₂ SO ₂ Me Et 1 HERE 12-175 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 HERE 12-176 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 HERE 12-177 OCH ₂ CH ₂ SO ₂ Me Me 2 HERE 12-178 OCH ₂ CH ₂ SO ₂ Me Et 2 HERE 12-179 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 HERE 12-180 OCH ₂ CH ₃ SO ₂ Me i-Pr 2 HERE 12-181 OMe Me 0 CCIa 12-102 OMe Et 0 CCI ₃ 12-183 OMe n-Pr 0 CCI ₃ 12-184 OMe i-Rr 0 CCI ₃ 12-185 OMe Me 1 CCI ₃ 12-186 OMe Et 1 CCI ₃ 12-187 OMe n-Pr 1 CCIa 12-188 OMe í-Pr 1 CCI ₃ 12-189 OMe Me 2 CCI ₃ 12-190 OMe Et 2 CCIa 12-191 OMe n-Pr 2 CCI ₃ 12-192 OMe i-Pr 2 CCI ₃ 12-193 OEt Me 0 CCIa 12-194 OEt Et 0 CCI ₃ 12-195 OEt n-Pr 0 CCI ₃

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Nr X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 12-196 OEt i-Pr 0 CCI ₃ 12-197 OEt Me 1 CCI ₃ 12-198 OEt Et 1 CCI ₃ 12-199 OEt n-Pr 1 CCI ₃ 12-200 OEt i-Pr 1 CCI, 12-201 OEt Me 2 CCI, 12-202 OEt Et 2 CCI ₃ 12-203 OEt n-Pr 2 CCI, 12-204 OEt i-Pr 2 CCI, 12-205 O - CH ₂ - c-Pr Me 0 CCI, 12-206 O-CHj-c-Pr Et 0 CCI, 12-207 O-CH ₂ -c-Pr n-Pr 0 CCI, 12-208 O - CH ₂ - c-Pr i-Pr 0 CCI, 12-209 CH ₂ -c-Pr Me 1 CCI, 12-210 O-CHj-o-Pr Et 1 CCI, 12-211 O - CH ₂ - c-Pr n-Pr 1 CCI ₃ 12-212 The —CH ₂ -c-Pr i-Pr 1 CCI ₃ 12-213 O-CH ₂ -c-Pr Me 2 CCÍ3 12-214 0 - CH ₂ - c-Pr Et 2 CCI ₃ 12-215 0 - CH ₂ - c-Pr n-Pr 2 CCI ₃ 12-216 0 - CHi - c-Pr i-Pr 2 CCI, 12-217 OCH ₂ CH ₂ OMe Me 0 CCI ₃ 12-218 OCH ₂ CHjOMe Et 0 CCI, 12-219 OCHjCHíOMe n-Pr 0 CClj 12-220 OCH ₂ CH ₂ OMe i-Pr 0 CCI ₃ 12-221 OCH ₂ CH ₂ OMe Me 1 CCI, 12-222 OCHjCHíOMe Et 1 CClj 12-223 OCH ₂ CH ₂ OMe n-Pr 1 CCI _S 12-224 OCH ₂ CH ₂ OMe i-Pr 1 CCI, 12-225 OCH ₂ CH ₂ OMe Me 2 CCI, 12-226 OCH ₂ CH ₂ OMe Et 2 CCI, 12-227 OCH ₂ CH ₂ OMe n-Pr 2 CCI, 12-228 OCH ₂ CH ₂ OMe i-Pr 2 CCI,

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Nr, X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-229 OCH ₂ CH ₂ SMe Me 0 CCIa 12-230 OCH ₂ CH ₂ SMe Et 0 CCI ₃ 12-231 OCH ₂ CH ₂ SMe n-Pr 0 CCI ₃ 12-232 OCH ₂ CH ₂ SMe i-Pr 0 CC1 ₃ 12-233 OCH ₂ CH ₂ SMe Me 1 CC1 ₃ 12-234 OCH ₂ CH ₂ SMe Et 1 CCIj 12-235 OCH ₂ CH ₂ SMe n-Pr 1 CCI ₃ 12-236 OCH ₂ CH ₂ SMe i-Pr 1 CCIj 12-237 OCH ₂ CH ₂ SMe Me 2 CCI ₃ 12-238 OCH ₂ CH ₂ SMe Et 2 CCI ₃ 12-239 OCH ₂ CH ₂ SMe n-Pr 2 CCIj 12-240 OCH ₂ CH ₂ SMe i-Pr 2 CCIj 12-241 OCH ₂ CH ₂ SO ₂ Me Me 0 CCIj 12-242 OCH ₂ CH ₂ S0 ₂ Me Et 0 CCIj 12-243 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CCIj 12-244 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CCI ₃ 12-245 OCH ₂ CH ₂ SO ₂ Me Me 1 CCI ₃ 12-246 OCH ₂ CH ₂ SO ₂ Me Et 1 CCI _a 12-247 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 CCI ₃ 12-248 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 cct ₃ 12-249 OCH ₂ CH ₂ SO ₂ Me Me 2 CCI ₃ 12-250 OCH ₂ CH ₂ SO ₂ Me Et 2 CCI ₃ 12-251 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 CCIj 12-252 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CCI ₃ 12-253 OMe Me 0 chf ₂ 12-254 OMe Et 0 chf ₂ 12-255 OMe n-Pr 0 chf ₂ 12-256 OMe i-Pr 0 chf ₂ 12-257 OMe Me 1 chf ₂ 12-258 OMe Et 1 chf ₂ 12-259 OMe n-Pr 1 chf ₂ 12-260 OMe i-Pr 1 CHF _a 12-261 OMe Me 2 chf ₂

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Nr X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-2S2 OMe Et 2 CHFj 12-263 OMe n-Pr 2 CHFj 12-254 OMe i-Pr 2 CHFí 12-265 OEt Me 0 CHFí 12-266 OEt Et 0 CHFí 12-267 OEt n-Pr 0 CHFí 12-258 OEt i-Pr D chf ₂ 12-269 OEt Me 1 CHF ₂ 12-270 OEt Et 1 CHFj 12-271 OEt n-Pr 1 CHFí 12-272 OEt i-Pr 1 CHF _Z 12-273 OEt Me 2 CHFí 12-274 OEt Et 2 CHFí 12-275 OEt n-Pr 2 CHFí 12-276 OEt i-Pr 2 CHF ₂ 12-277 0 - CH ₅ - c-Pr Me 0 CHFj 12-278 0 - CHi - c-Pr Et 0 CHFí 12-279 0 - CH ₂ - c-Pr n-Pr 0 CHF ₂ 12-260 O - CH ₂ - c-Pr i-Pr 0 CHFí 12-281 O - CHí - c-Pr Me 1 CHFí 12-282 O - CH ₂ - c-Pr Et 1 CHFí 12-2B3 O - CH ₂ - c-Pr n-Pr 1 CHF ₂ 12-284 O - CHí - c-Pr i-Rr 1 CHFí 12-285 The —CH ₂ -c-Pr Me 2 CHFí 12-286 O - CH ₂ - c-Pr Et 2 CHFí 12-287 O-CHi-c-Pr n-Pr 2 CHF ₂ 12-288 O - CH ₂ - c-Pr í-Pr 2 CHFí 12-289 OCH ₂ CHiOMe Me 0 CHFí 12-290 OCHiCHiOMe Et 0 CHF ₂ 12-291 OCH ₂ CH ₂ OMe n-Pr 0 CHFí 12-292 OCHiCHiOMe i-Rr 0 CHF ₂ 12-293 OCHiCHiOMe Me 1 CHFí 12-294 OCH ₃ CHiOMe Et 1 CHFí

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-295 OCH ₂ CH ₂ OMe n-Pr 1 chf ₂ 12-296 OCHjCHjOMe í-Pr 1 chf ₂ 12-297 OCH ₂ CH ₂ OMe Me 2 chf ₂ 12-298 OCH ₂ CH ₂ OMe Et 2 CHFj 12-299 OCH ₂ CH ₂ OMe n-Pr 2 chf ₂ 12-300 OCHjCHjOMe i-Pr 2 chf ₂ 12-301 OCH ₂ CH ₂ SMe Me 0 chf ₂ 12-302 OCH ₂ CH ₂ SMe Et 0 chf ₂ 12-303 OCH ₂ CH ₂ SMe n-Pr O chf ₂ 12-304 OCH ₂ CH ₂ SMe i-Pr 0 chf ₂ 12-305 OCH ₂ CH ₂ SMe Me 1 chf ₂ 12-306 OCH ₂ CH ₂ SMe Et 1 chf ₂ 12-307 OCH ₂ CH ₂ SMe n-Pr 1 chf ₂ 12-308 OCH ₂ CH ₂ SMe i-Rr 1 chf ₂ 12-309 OCH ₂ CH ₂ SMe Me 2 chf ₂ 12-310 OCH ₂ CH ₂ SMe Et 2 chf ₂ 12-311 OCH ₂ CH ₂ SMe n-Pr 2 chf ₂ 12-312 OCH ₂ CH ₂ SMe i-Pr 2 chf ₂ 12-313 OCH ₂ CH ₃ SO ₂ Me Me O chf ₂ 12-314 OCH ₂ CH ₂ SO ₂ Me Et 0 chf ₂ 12-315 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 chf ₂ 12-316 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 chf ₂ 12-317 OCH ₂ CH ₂ SO ₂ Me Me 1 chf ₂ 12-318 OCH ₂ CH ₂ SO ₂ Me Et 1 chf ₂ 12-319 OCH ₂ CH ₂ SO ₂ Me n-Pr 1 chf ₂ 12-320 OCH ₂ CH ₂ SO ₂ Me i-Pr 1 chf ₂ 12-321 OCH ₂ CH ₂ SO ₂ Me Me 2 CHFj 12-322 OCH ₂ CH ₂ SO ₂ Me Et 2 chf ₂ 12-323 OCH ₂ CH ₂ SO ₂ Me n-Pr 2 chf ₂ 12-324 OCH ₂ CH _z SO ₂ Me i-Pr 2 chf ₂ 12-325 OMe Me 0 CF (CF ₃ ) ₂ 12-326 OMe Et 0 CF (CF ₃ ) ₂ 12-327 OMe n-Pr 0 CF (CF ₃ ) ₂

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Nr. X R ¹ π Y Physical data: ¹ H-NMR: δ [CDCIs] 12-328 OMe i-Pr 0 CF (CF ₃ ) ₂ 12-329 OMe Me 1 CF (CF ₃ ) ₂ 12-330 OMe Et 1 CF (CF ₃ ) ₂ 12-331 OMe n-Pr 1 CF (CF ₃ } ₂ 12-332 OMe i-Pr 1 CF (CF ₃ } ₂ 12-333 OMe Me 2 CF (CF ₃ ) ₂ 12-334 OMe Et 2 CF (CF ₃ ) ₂ 12-335 OMe n-Pr 2 CF (CF ₃ ) ₂ 12-336 OMe i-Pr 2 CF (CF ₃ ) ₂ 12-337 OEt Me 0 CF (CF ₃ ) ₂ 12-338 OEt Et 0 CF (CF ₃ ) ₂ 12-339 OEt n-Pr 0 CF (CF ₃ ) ₂ 12-340 OEt i-Pr 0 CF (CF ₃ ) ₂ 12-341 OEt Me 1 CF (CF ₃ ) ₂ 12-342 OEt Et 1 CF (CF ₃ ) ₂ 12-343 OEt n-Pr 1 CF (CF ₃ ) ₂ 12-344 OEt í-Pr 1 CF (CF ₃ ) ₂ 12-345 OEt Me 2 CF (CF ₃ ) ₂ 12-346 OEt Et 2 CF (CF ₃ ) ₂ 12-347 OEt n-Rr 2 CF (CF ₃ ) ₂ 12-34S OEt i-Pr 2 CF (CFj) ₂ 12-349 O-CH ₂ -c-Pr Me 0 CF (CF ₃ ) ₂ 12-350 O - CH ₂ - c-Pr Et 0 CF (CF ₃ ) ₂ 12-351 O-CH ₂ -c-Pr n-Pr 0 CF (CF ₃ ) ₂ 12-352 O-CH ₂ -c-Pr i-Pr 0 CF (CF ₃ ) ₂ 12-353 O- CH ₅ -c-Pr Me 1 CF (CF ₃ ) ₂ 12-354 O - CH ₂ - c-Pr Et 1 CF (CF ₃ ) ₂ 12-355 O - CH ₂ - c-Pr n-Pr 1 CF (CF ₃ ) ₂ 12-356 O - CH ₂ - c-Pr i-Pr 1 CF (CF ₃ ) ₂ 12-357 O - CH ₂ - c-Pr Me 2 CF (CF ₃ ) ₂ 12-358 O - CH ₂ c-Pr Et 2 CF (CF ₃ ) ₂ 12-359 O - CH ₂ - c-Pr n-Pr 2 CF (CF ₃ } ₂ 12-360 O-CH ₂ -c-Pr i-Pr 2 CF (CF ₃ } ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] ....... - L 12-361 OCHjCHjOMe Me 0 CF (CF ₃ ) ₂ 12-362 OCHjCHjOMe Et 0 CF (CF ₃ ) ₂ 12-363 OCH ₂ CH ₂ OMe n-Pr 0 CF (CF ₃ ) ₂ 12-364 OCHiCHjOMe i-Pr 0 CF (CF ₃ ) ₂ 12-365 OCH ₂ CH ₂ OMe Me 1 CF (CF ₃ ) ₂ 12-366 OCH ₂ CH ₂ OMe Et 1 CF (CF ₃ ) ₂ 12-367 OCH ₂ CH ₂ OMe n-Pr 1 CF (CF ₃ ) ₂ 12-363 OCH ₂ CH ₂ OMe í-Pr 1 CF (CF ₃ ) ₂ 12-369 OCH ₂ CH ₂ OMe Me 2 CF (CF ₃ ) ₂ 12-370 OCH ₂ CH ₂ OMe Et 2 CF (CF ₃ ) ₂ 12-371 OCK ₂ CH ₂ OMe n-Pr 2 CF (CF ₃ ) ₂ 12-372 OCH ₂ CH ₂ OMe i-Pr 2 CF (CF ₃ ) ₂ 12-373 OCH ₂ CH ₂ SMe Me 0 CF (CF ₃ ) ₂ 12-374 OCH ₂ CH ₂ SMe Et 0 CF <CF ₃ ) ₂ 12-375 OCH ₂ CH ₂ SMe n-Pr 0 CF (CF _a ) ₂ 12-376 OCH ₂ CH ₂ SMe i-Pr 0 CF (CF ₃ ) ₂ 12-377 OCH ₂ CH ₂ SMe Me 1 CF (CF ₃ ) ₂ 12-373 OCH ₂ CH ₂ SMe Et 1 CF (CF ₃ ) ₂ 12-379 OCH ₂ CH ₂ SMe n-Pr 1 CF (CF ₃ ) ₂ 12-380 OCH ₂ CH ₂ SMe i-Pr 1 CF (CF ₃ ) ₂ 12-381 OCH ₂ CH ₂ SMe Me 2 CF (CF ₃ ) ₂ 12-382 OCH ₂ CH ₂ SMe Et 2 CF (CF ₃ ) ₂ 12-383 OCHjCHjSMe n-Pr 2 CF (CF ₃ ) ₂ 12-384 OCH ₂ CH ₂ SMe i-Pr 2 CF (CF ₃ ) ₂ 12-385 OCH ₂ CH ₂ SO ₂ Me Me 0 CF (CF ₃ ) ₂ 12-386 OCH ₂ CH ₂ SO ₂ Me Et 0 CF (CF ₃ ) ₂ 12-387 OCH ₂ CH ₂ SO ₂ Me n-Pr 0 CF (CF ₃ ) ₂ 12-388 OCH ₂ CH ₂ SO ₂ Me i-Pr 0 CF (CF ₃ ) ₂ 12-389 OCH ₂ CH ₂ SO ₂ Me Me 1 CF (CFj) ₂ 12-390 OCH ₂ CH ₂ SO ₂ Me Et 1 CF (CF ₃ ) j 12-391 OCH ₂ CH ₂ S0 ₂ Me n-Pr 1 CF (CF ₃ ) ₂ 12-392 OCH ₂ CH ₂ S0 ₂ Me i-Pr 1 CF (CF ₃ ) ₂ 12-393 OCH ₂ CH ₂ SO ₃ Me Me 2 CF (CF ₃ ) ₂

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Nr. X R ¹ n Y Physical data: ¹ H-NMR: δ [CDCIs] 12-394 OCH ₂ CH ₂ SO ₂ Me Et 2 cf (cf,> ₂ 12-395 OCHjCH ₂ SO ₂ Me n-Pr 2 CF (CF,) ₂ 12-396 OCH ₂ CH ₂ SO ₂ Me i-Pr 2 CF (CF ₃ } ₂

B. Formulation examples

a) a powder is obtained by mixing and grinding in a hammer mill of 10 parts by weight of a compound of formula (I) and / or its salts and 90 parts by weight of talc as an inert substance.

b) a powder that can be humidified and easily dispersible in water is obtained by mixing and grinding in a pin mill of 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of quartz containing kaolin and 1 part by weight of oleyl methyl taurinic acid as a humidifier and dispersant.

c) a dispersion concentrate easily dispersible in water is obtained by mixing and grinding in a ball mill, in a fineness less than 5 microns, of 20 parts by weight of a compound of formula (I) and / or its salts with 6 parts by weight of alkylphenol polyglycolether (®Triton X 207), 3 parts by weight of isotridecanol polyglycolether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, from about 255 to 277C).

d) an emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) and / or its salts, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

e) a water-dispersible granule is obtained by mixing and grinding in a pin mill of parts by weight of a compound of formula (I) and / or its salts, parts by weight of calcium lignosulfonate, parts by weight of sodium lauryl sulfate, parts by weight of polyvinyl alcohol and

7 parts by weight of kaolin, and the powder is granulated in a fluidized bed by spraying water as a granulated liquid.

f) a water-dispersible granule is also obtained through the homogenization and pre-crushing of

25 parts by weight of a compound of the formula (I) and / or its salts, parts by weight of 2,2'-dinaftilmetan-6'6-disulgone sodium, parts by weight of oleoylmethyl sodium of taurinic acid,

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109/110 parts by weight of polyvinyl alcohol, parts by weight of calcium carbonate and 50 parts by weight of water then, by grinding in a hammer mill, then the suspension obtained in this way is sprayed and dried in a spray tower by through a material spray nozzle.

C. Biological example

1. Herbicidal effect against harmful plants in the pre-emergence

Seeds of cultivation plants or mono or dicot weeds are placed in wooden fiber pots on sandy soil and covered with soil. The compounds according to the invention formulated in the form of powder spray (WP) or as emulsifiable concentrates (EC) are applied as an aqueous suspension or as an emulsion with a water application rate equivalent to 600 to 800 l / ha by the use of 0.2% of humectant on the surface of the covering earth. After the treatment, the pots are placed in greenhouses and maintained in good growth conditions for the test plants. Visual scoring of damage to experimental plants occurs after a 3-week trial period compared to untreated controls (percentage herbicidal effect (%): 100% effect = dead plants, 0% = as control plants). In this sense, compounds number 1-21, 5-17, as well as 5-21 show, for example, at a respective application rate of 80 g / ha, at least 90% effect against Abutilon theophrasti and Veronica persica. Compounds number 2-21, as well as 2-17 show, at an application rate of the respective 80 g / ha, at least 90% effect against Alopecurus myosuroides, Amaranthus retroflexus and Veronica persica.

Herbicidal effect against harmful plants in post-emergence

Seeds of cultivation plants or mono or dicot weeds are placed in wooden fiber pots in sandy clay, covered with soil and placed in greenhouses under good growing conditions. 2 to 3 weeks after sowing the experimental plants are treated in the single leaf stage. The compounds according to the invention formulated in powder form (WP) or as emulsifiable concentrates (EC) are sprayed as an aqueous suspension or as an emulsion with a water application rate equivalent to 600 to 800 l / ha by using 0.2% of humectant on the green parts of the plants. After about 3 weeks of waiting time in greenhouses of experimental plants and under ideal growing conditions the effect of the preparation is scored visually compared to untreated controls (percentage herbicidal effect (%): 100% effect = dead plants, 0% = as control plants). In this sense, compounds number 3-17, 5-21, as well as 2-17 show, for example, at a respective application rate of 80 g / ha, at least 90% effect against

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Avena fetua, Matricaria inodora and Viola tricolor. Compounds number 1-13, 1-17, 1-21, as well as 2-21 show, at an application rate of the respective 80 g / ha, at least 90% effect against Echinochloa crus galli, Pharbitis purpureum and Stellaria media.

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Claims (9)

1. 2- (3-acylthiobenzoyl) cyclohexanediones of formula (I) or their salts, characterized by SO R (D. on what R ¹ means (C 1 -C 6) -alkyl, R ² means hydroxyl, SR ¹³ , NR ¹⁴ R ¹⁵ , R ³ and R ⁸ independently mean hydrogen or (C 1 -C 4) -alkyl, or the radicals R ³ and R ⁸ together form the unit Z, which represents an oxygen or sulfur atom, or represents one to four methylene groups, R ⁴ and R ⁷ mean, independently of each other, hydrogen or (C 1 -C 4) -alkyl, R ⁵ and R ⁶ mean, independently of each other, hydrogen or (C 1 -C 4) -alkyl, or form, together with the carbon atom to which they are attached, a carbonyl group, X stands for OR ⁹ , OCOR ⁹ , OSO ₂ R ¹⁰ , R ⁹ means hydrogen, (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl or phenyl- (C1-C6) -alkyl, in which the last six radicals mentioned are replaced by radicals from the group consisting of halogen, OR ¹¹ and S (O) mR ¹² , R ¹⁰ means (C1-Cej-alkyl, (C2-C6) -alkenyl, (C2-C6) -alkynyl, (C3-Ce) cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl or phenyl - (Ci-C6) -alkyl, in which the last six radicals mentioned are replaced by radicals from the group consisting of halogen, OR ¹¹ and S (O) mR ¹² , R ¹¹ means hydrogen, (C1-C6) -alkyl, (C2-C6) -alkenyl or (C2-C6) alkynyl, R ¹² stands for (C1-C6) -alkyl, (C2-C6) -alkenyl or (C2-C6) -alkynyl, R ¹³ means (C1-C4) -alkyl, phenyl substituted by radicals of the group consisting of nitro, cyano, (C1-C4) -alkyl, (C1-C4) -haloalkyl, (C1-C4) -alkoxy or (C1C4 ) -haloalkoxy or means phenyl partially or completely halogenated, R ¹⁴ means hydrogen, (C1-C4) -alkyl or (C1-C4) -alkoxy, R ¹⁵ means hydrogen or (C 1 -C 4) -alkyl, or Petition 870180037453, of 05/07/2018, p. 122/128 2/3 R ¹⁴ and R ¹⁵ form, with the nitrogen atom to which they are attached, an unsaturated, partially saturated or saturated 5- or 6-membered ring, which contains zero, one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen , which is replaced by radicals from the group consisting of cyano, halogen, (C1C4) -alkyl, (C1-C4) -haloalkyl, (C1-C4) -alkoxy and (C1-C4) -haloalkoxy, Y means (C1-C6) -haloalkyl, m means 0, 1 or 2, n means 0, 1 or 2, s means 0, 1, 2 or 3. 2. 2- (3-acylthiobenzoyl) cyclohexanediones according to claim 1, characterized by R ¹ means methyl, ethyl, n-propyl or iso-propyl, R ² means hydroxyl, R ³ and R ⁸ mean, independently of each other, hydrogen or (C1-C4) alkyl, or the radicals R ³ and R ⁸ together form a methylene or ethylene group, R ⁴ and R ⁷ mean, independently of each other, hydrogen, methyl or ethyl, R ⁵ and R ⁶ mean, independently of one another, hydrogen, methyl or ethyl, X stands for OR ⁹ , OCOR ⁹ , OSO2R ¹⁰ , R ⁹ stands for cyclopropylmethyl or (C1-C6) -alkyl substituted by methoxy or ethoxy groups, R ¹⁰ stands for (C1-C6) -alkyl substituted by methoxy or ethoxy groups, Y means (C1-C6) -haloalkyl, n means 0, 1 or 2, s means 0, 1,2 or 3. 2. 2- (3-hereiobenzoyl) cyclohexanediones according to claim 1 or 2, characterized by R ¹ means methyl, ethyl, n-propyl or iso-propyl, R ² means hydroxyl, R ³ and R ⁸ mean, independently of each other, hydrogen, methyl or ethyl, or the radicals R ³ and R ⁸ together form a methylene or ethylene group, R ⁴ and R ⁷ mean, independently of each other, hydrogen, methyl or ethyl, R ⁵ and R ⁶ mean, independently of each other, hydrogen, methyl or ethyl, X stands for OR ⁹ , R ⁹ means cyclopropylmethyl, or ethyl or methyl substituted by methoxy or ethoxy groups, Petition 870180037453, of 05/07/2018, p. 123/128 3/3 Y means trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoro sopropyl, n means 0, 1 or 2, s means 0, 1,2 or 3. 4. Herbicidal products, characterized in that they comprise 0.1 to 95% by weight of a compound of formula (I) as defined in any one of claims 1 to 3. 5. Herbicidal products according to claim 4, characterized in that they are mixed with inert materials, surfactants, solvents and other additional substances. Use of compounds of formula (I) as defined in any one of claims 1 to 3, characterized in that they are for the control of unwanted plants. Use according to claim 6, characterized in that the compounds of formula (I) are used for the control of unwanted plants in crops of cultivation plants. Use according to claim 7, characterized in that the crop plants are transgenic crop plants. Compound, characterized in that it has the formula (II) (H) in which X, Y, R ^{1 and} n are as defined in any one of claims 1 to 3. Petition 870180037453, of 05/07/2018, p. 124/128